907606-68-2

Basic information

• Product Name: (3aR,6aS)-1-(tert-butoxycarbonyl)octahydrocyclopenta[c]pyrrol-2-iuM carboxyfor
• Synonyms: (3aR,6aS)-1-(tert-butoxycarbonyl)octahydrocyclopenta[c]pyrrol-2-iuM carboxyfor;(1S,3aR,6aS)-Octahydrocyclopenta[c]pyrrole-1-carboxylic acid tert-butyl ester oxalate;Cyclopenta[c]pyrrole-1-carboxylic acid, octahydro-, 1,1-diMethylethyl ester, (1S,3aR,6aS)-, ethanedioate (1:1);Cyclopenta[c]pyrrole-1-carboxylic acid, octahydro-, 1,1-diMethylethyl ester, (1S,3aR,6aS)-, ethanedioate;(1S,3aR,6aS)-tert-Butyl octahydrocyclopenta[c]pyrrole-1-carboxylate oxalate;(3aR,6aS)-1-(tert-Butoxycarbonyl)octahydrocyclopenta[c]pyrroliuM oxalate;2-Methyl-2-propanyl (1S,3aR,6aS)-octahydrocyclopenta[c]pyrrole-1-carboxylate ethanedioate (1:1);(1S,3aR,6aS)-Octahydrocyclopenta[c]pyrrole-1-carboxylic acid t-butyl ester oxalate
• CAS NO: 907606-68-2
• Molecular Formula: C₂H₂O₄*C₁₂H₂₁NO₂
• Molecular Weight: 301.33552
• Mol File: 907606-68-2.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• Density: 1.26 at 20℃
• Vapor Pressure: 0Pa at 25℃
• Storage Temp.: 2-8°C
• CAS DataBase Reference: (3aR,6aS)-1-(tert-butoxycarbonyl)octahydrocyclopenta[c]pyrrol-2-iuM carboxyfor(CAS DataBase Reference)
• NIST Chemistry Reference: (3aR,6aS)-1-(tert-butoxycarbonyl)octahydrocyclopenta[c]pyrrol-2-iuM carboxyfor(907606-68-2)
• EPA Substance Registry System: (3aR,6aS)-1-(tert-butoxycarbonyl)octahydrocyclopenta[c]pyrrol-2-iuM carboxyfor(907606-68-2)

Safety Data

• Hazardous Substances Data: 907606-68-2(Hazardous Substances Data)

Usage

General Description

The chemical "(3aR,6aS)-1-(tert-butoxycarbonyl)octahydrocyclopenta[c]pyrrol-2-iuM carboxyfor" is a compound with a molecular formula of C15H25NO3. It is a carboxylic acid derivative with a tert-butoxycarbonyl group attached to the octahydrocyclopenta[c]pyrrol-2-iuM moiety. (3aR,6aS)-1-(tert-butoxycarbonyl)octahydrocyclopenta[c]pyrrol-2-iuM carboxyfor is commonly used in organic synthesis as a protecting group for amines and as a reagent in peptide synthesis. It is also used in pharmaceutical research and development as a building block for the synthesis of various compounds. The (3aR,6aS)-1-(tert-butoxycarbonyl)octahydrocyclopenta[c]pyrrol-2-iuM carboxyfor is a versatile compound with potential applications in various fields including drug discovery, chemical research, and material science.

Synthetic route

(1S,3aR,6aS)-2-(tert-butoxycarbonyl)octahydrocyclopenta[c]pyrrole-1-carboxylic acid (S)-1,2,3,4-tetrahydro-1-naphthylammonium salt (1227704-10-0) + oxalic acid (144-62-7) + tert-butyl alcohol (75-65-0) → tert-butyl (1S,3aR,6aS)-octahydrocyclopenta[c]pyrrole-1-carboxylate oxalic acid salt (907606-68-2)

Conditions

Yield

Stage #1: (1S,3aR,6aS)-2-(tert-butoxycarbonyl)octahydrocyclopenta[c]pyrrole-1-carboxylic acid (S)-1,2,3,4-tetrahydro-1-naphthylammonium salt With sodium hydrogen sulfate In tert-butyl methyl ether; water for 0.5h; Stage #2: tert-butyl alcohol With dmap; sodium hydrogen sulfate; di-tert-butyl dicarbonate In tert-butyl methyl ether; water at 20 - 25℃; for 5 - 6h; Stage #3: oxalic acid With methanesulfonic acid; potassium carbonate Product distribution / selectivity; more than 3 stages;

81%

acetic acid tert-butyl ester (540-88-5) + (1R,3aR,6aS)-octahydrocyclopenta[c]pyrrole-1-carboxylic acid hydrochloride + oxalic acid (144-62-7) → tert-butyl (1S,3aR,6aS)-octahydrocyclopenta[c]pyrrole-1-carboxylate oxalic acid salt (907606-68-2)

Conditions	Yield
Stage #1: acetic acid tert-butyl ester; (1R,3aR,6aS)-octahydrocyclopenta[c]pyrrole-1-carboxylic acid hydrochloride In dichloromethane at 0 - 21℃; Stage #2: With methanesulfonic acid In dichloromethane; water at 0 - 21℃; for 18.25h; Sealed tube; Stage #3: oxalic acid	59.7%

acetic acid tert-butyl ester (540-88-5) + (1S,3αR,6αS)-octahydrocyclopenta[c]pyrrole-1-carboxylate hydrochloride (1205676-44-3) + oxalic acid (144-62-7) → tert-butyl (1S,3aR,6aS)-octahydrocyclopenta[c]pyrrole-1-carboxylate oxalic acid salt (907606-68-2)

Conditions	Yield
Stage #1: acetic acid tert-butyl ester; (1S,3αR,6αS)-octahydrocyclopenta[c]pyrrole-1-carboxylate hydrochloride With methanesulfonic acid In chloroform at 0 - 25℃; for 18h; Stage #2: oxalic acid In isopropyl alcohol at 75 - 80℃; for 0.5h;	0.08 g

(1S,3aR,6aS)-octahydrocyclopenta[c]pyrrole-1-carbonitrile (1205676-37-4) → tert-butyl (1S,3aR,6aS)-octahydrocyclopenta[c]pyrrole-1-carboxylate oxalic acid salt (907606-68-2)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: water; hydrogenchloride / methanol / 24 h / Reflux 2.1: methanesulfonic acid / chloroform / 18 h / 0 - 25 °C 2.2: 0.5 h / 75 - 80 °C View Scheme

(1S,3aR,6aS)-di-tert-butyl hexahydrocyclo-penta[c]pyrrol-1,2(1H)-dicarboxylate (402960-06-9) → tert-butyl (1S,3aR,6aS)-octahydrocyclopenta[c]pyrrole-1-carboxylate oxalic acid salt (907606-68-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: methanesulfonic acid / tetrahydrofuran / 12 h / 22 - 27 °C / Industrial scale 2: tert-butyl methyl ether; Isopropyl acetate / 2.5 h / Industrial scale View Scheme

di-tert-butyl dicarbonate (24424-99-5) → tert-butyl (1S,3aR,6aS)-octahydrocyclopenta[c]pyrrole-1-carboxylate oxalic acid salt (907606-68-2)

Conditions	Yield
Multi-step reaction with 3 steps 1: dmap / tert-butyl methyl ether; tert-butyl alcohol / 6 h / 22 - 27 °C / Industrial scale 2: methanesulfonic acid / tetrahydrofuran / 12 h / 22 - 27 °C / Industrial scale 3: tert-butyl methyl ether; Isopropyl acetate / 2.5 h / Industrial scale View Scheme

tert-butyl (1S,3aR,6aS)-octahydrocyclopenta[c]pyrrole-1-carboxylate (714194-68-0) + oxalic acid (144-62-7) → tert-butyl (1S,3aR,6aS)-octahydrocyclopenta[c]pyrrole-1-carboxylate oxalic acid salt (907606-68-2)

Conditions	Yield
In tert-butyl methyl ether; Isopropyl acetate for 2.5h; Industrial scale;	82 kg

tert-butyl (1S,3aR,6aS)-octahydrocyclopenta[c]pyrrole-1-carboxylate oxalic acid salt (907606-68-2) → tert-butyl (1S,3aR,6aS)-octahydrocyclopenta[c]pyrrole-1-carboxylate (714194-68-0)

Conditions	Yield
With potassium carbonate In Isopropyl acetate; water at 20 - 25℃; for 0.5 - 3h; Product distribution / selectivity;
With potassium carbonate In Isopropyl acetate; water at 20 - 25℃; for 3h; Product distribution / selectivity;
With potassium carbonate In Isopropyl acetate; water at 20℃; for 3h; Product distribution / selectivity;

tert-butyl (1S,3aR,6aS)-octahydrocyclopenta[c]pyrrole-1-carboxylate oxalic acid salt (907606-68-2) → (1S,3aR,6aS)-tert-butyl 2-((S)-2-(benzyloxycarbonylamino)-3,3-dimethylbutanoyl)octahydrocyclopenta[c]pyrrole-1-carboxylate (926276-15-5)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: potassium carbonate / water; Isopropyl acetate / 3 h / 20 °C 2.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / water; Isopropyl acetate / 6 h / 0 - 5 °C 2.2: 20 - 25 °C View Scheme

tert-butyl (1S,3aR,6aS)-octahydrocyclopenta[c]pyrrole-1-carboxylate oxalic acid salt (907606-68-2) → (1S,3aR,6aS)-tert-butyl 2-((S)-2-amino-3,3-dimethylbutanoyl)octahydrocyclopenta[c]pyrrole-1-carboxylate (926276-16-6)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: potassium carbonate / water; Isopropyl acetate / 3 h / 20 - 25 °C 2.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / water; Isopropyl acetate / 6 h / 0 - 5 °C / Inert atmosphere 2.2: 20 - 25 °C 3.1: hydrogen / 10 wt% Pd(OH)2 on carbon / water; Isopropyl acetate / 1 h / 20 °C / 2311.54 Torr View Scheme
Multi-step reaction with 3 steps 1.1: potassium carbonate / water; Isopropyl acetate / 3 h / 20 °C 2.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / water; Isopropyl acetate / 6 h / 0 - 5 °C 2.2: 20 - 25 °C 3.1: hydrogen / 10 wt% Pd(OH)2 on carbon / Isopropyl acetate / 1 h / 20 °C / 2311.54 Torr View Scheme

Upstream product

• 714194-68-0 tert-butyl (1S,3aR,6aS)-octahydrocyclopenta[c]pyrrole-1-carboxylate 
• 144-62-7 oxalic acid 
• 24424-99-5 di-tert-butyl dicarbonate 
• 402960-06-9 (1S,3aR,6aS)-di-tert-butyl hexahydrocyclo-penta[c]pyrrol-1,2(1H)-dicarboxylate 
• 1205676-37-4 (1S,3aR,6aS)-octahydrocyclopenta[c]pyrrole-1-carbonitrile 
• 540-88-5 acetic acid tert-butyl ester 
• 1205676-44-3 (1S,3αR,6αS)-octahydrocyclopenta[c]pyrrole-1-carboxylate hydrochloride 
• 1227704-10-0 (1S,3aR,6aS)-2-(tert-butoxycarbonyl)octahydrocyclopenta[c]pyrrole-1-carboxylic acid (S)-1,2,3,4-tetrahydro-1-naphthylammonium salt 
• 75-65-0 tert-butyl alcohol 
• 1219204-23-5 (1R,3aR,6aS)-octahydrocyclopenta[c]pyrrole-1-carboxylic acid hydrochloride 

Downstream Products

• 926276-15-5 (1S,3aR,6aS)-tert-butyl 2-((S)-2-(benzyloxycarbonylamino)-3,3-dimethylbutanoyl)octahydrocyclopenta[c]pyrrole-1-carboxylate 
• 714194-68-0 tert-butyl (1S,3aR,6aS)-octahydrocyclopenta[c]pyrrole-1-carboxylate 

Relevant articles and documents

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Compound (1) or a salt that is useful as an intermediate for the production of a medicine, an agrochemical or the like can be produced by a process including the following steps: (A) reacting an aldehyde (2) with nitromethane to produce a nitroaldehyde; (B) reacting the nitroaldehyde with an alcohol to produce a nitroacetal; (C) reducing the nitroacetal to produce an aminoacetal; (D) protecting an amino group in the aminoacetal to produce a protected aminoacetal; (E) treating the protected aminoacetal with an acid and subsequently with a base and then reacting the resultant product with a cyanating agent to produce a nitrile; (F) hydrolyzing the nitrile to produce a protected amino acid; and (G) substituting a group R5 in the protected amino acid by a hydrogen atom and protecting a carboxyl group therein.

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