(4aS,7aS)-tert-Butyl octahydro-1H-pyrrolo[3,4-b]pyridine-1-carboxylate

Base Information

• Chemical Name: (4aS,7aS)-tert-Butyl octahydro-1H-pyrrolo[3,4-b]pyridine-1-carboxylate
• CAS No.: 159991-07-8
• Molecular Formula: C12H22N2O2
• Molecular Weight: 226
• European Community (EC) Number: 812-248-4,812-932-2
• DSSTox Substance ID: DTXSID30364041
• Wikidata: Q76139756
• Mol file: 159991-07-8.mol

Synonyms:159991-07-8;(4aS,7aS)-tert-Butyl octahydro-1H-pyrrolo[3,4-b]pyridine-1-carboxylate;tert-butyl (4aS,7aS)-2,3,4,4a,5,6,7,7a-octahydropyrrolo[3,4-b]pyridine-1-carboxylate;tert-butyl (4aS,7aS)-octahydro-1H-pyrrolo[3,4-b]pyridine-1-carboxylate;(4AS,7AS)-TERT-BUTYL OCTAHYDROPYRROLO[3,4-B]PYRIDINE-1-CARBOXYLATE;cis-(4aS,7aS)-1-Boc-Octahydro-1H-pyrrolo[3,4-b]pyridine;1-Boc-1H-octahydro-pyrrolo[3,4-b]pyridine;tert-Butyl cis-octahydro-1H-pyrrolo[3,4-b]pyridine-1-carboxylate;CS-WAA0287;SCHEMBL1983358;DTXSID30364041;1H-Pyrrolo[3,4-b]pyridine-1-carboxylic acid, octahydro-, 1,1-dimethylethyl ester, (4aS,7aS)-;AMY21554;MFCD11973767;MFCD12198664;(4aS,7aS)-tert-Butyloctahydro-1H-pyrrolo[3,4-b]pyridine-1-carboxylate;DS-15227;EN300-702669;P11285;P17260;A883251;(S,S)-1-t-butoxycarbonyloctahydropyrrolo[3.4-b]pyridine;(4aS,7aS)-1-t-Butoxycarbonyloctahydropyrrolo[3.4-b]pyridine;(S,S)-2-tert-butoxycarbonyl-2,8-diazabicyclo[4.3.0]nonane;[1S,6S]-2-tertbutyloxycarbonyl-2,8-diazabicyclo[4,3,0]nonane;t-Butyl cis-octahydro-1H-pyrrolo[3,4-b]pyridine-1-carboxylate;1,1-dimethylethyl (4aS,7aS)-octahydro-1H-pyrrolo[3,4-b]pyridine-1-carboxylate

Chemical Property of (4aS,7aS)-tert-Butyl octahydro-1H-pyrrolo[3,4-b]pyridine-1-carboxylate

Chemical Property:

• Boiling Point: 313.8±15.0 °C(Predicted)
• PKA: 10.66±0.20(Predicted)
• PSA: 41.57000
• Density: 1.052±0.06 g/cm3(Predicted)
• LogP: 1.87200
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 226.168127949
• Heavy Atom Count: 16
• Complexity: 273

Purity/Quality:

98%min ^*data from raw suppliers

(4aS,7aS)-tert-Butyloctahydro-1H-pyrrolo[3,4-b]pyridine-1-carboxylate 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)N1CCCC2C1CNC2
• Isomeric SMILES: CC(C)(C)OC(=O)N1CCC[C@@H]2[C@H]1CNC2

Technology Process of (4aS,7aS)-tert-Butyl octahydro-1H-pyrrolo[3,4-b]pyridine-1-carboxylate

There total 2 articles about (4aS,7aS)-tert-Butyl octahydro-1H-pyrrolo[3,4-b]pyridine-1-carboxylate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 86.8%

(4aS,7aS)-tert-butyl 6-benzyloctahydro-1H-pyrrolo[3,4-b]pyridine-1-carboxylate (159991-06-7) → tert-butyl (4aS,7aS)-octahydro-1H-pyrrolo[3,4-b]pyridine-1-carboxylate (159991-07-8)

Guidance literature:

With hydrogen; palladium 10% on activated carbon; In methanol; for 10h; under 2280.15 Torr;

Reference yield:

(S,S)-8-benzyl-2,8-diazabicyclo[4.3.0]nonane-D-tartrate (151213-39-7,128740-14-7,161594-54-3) + di-tert-butyl dicarbonate (24424-99-5) → tert-butyl (4aS,7aS)-octahydro-1H-pyrrolo[3,4-b]pyridine-1-carboxylate (159991-07-8)

Guidance literature:

Multi-step reaction with 2 steps

1: triethylamine / dichloromethane / 20 °C

2: hydrogen / 10 wt% Pd(OH)2 on carbon / methanol / 3 h / 20 °C / 1551.49 Torr

With hydrogen; triethylamine; 10 wt% Pd(OH)2 on carbon; In methanol; dichloromethane;

Reference yield:

2-(3,3-bis(4-fluorophenyl)-2-oxopyrrolidin-1-yl)acetic acid (1219624-45-9) + tert-butyl (4aS,7aS)-octahydro-1H-pyrrolo[3,4-b]pyridine-1-carboxylate (159991-07-8) → C30H35F2N3O4 (1219626-53-5)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; HATU; In dichloromethane; at 20 ℃;

upstream raw materials:

(4aS,7aS)-tert-butyl 6-benzyloctahydro-1H-pyrrolo[3,4-b]pyridine-1-carboxylate

(S,S)-8-benzyl-2,8-diazabicyclo[4.3.0]nonane-D-tartrate

di-tert-butyl dicarbonate

Downstream raw materials:

C₃₀H₃₅F₂N₃O₄

Refernces

• 1、 -. "NOVEL COMPOUNDS AS CALCIUM CHANNEL BLOCKERS". Page/Page column 88. . Retrieved 2010/04/27.
• 2、 -. "Bicyclic amine derivatives". . . Retrieved 2008/06/13.