(1S,3aR,6aS)-tert-butyl 2-((S)-2-(benzyloxycarbonylamino)-3,3-dimethylbutanoyl)octahydrocyclopenta[c]pyrrole-1-carboxylate

Base Information

• Chemical Name: (1S,3aR,6aS)-tert-butyl 2-((S)-2-(benzyloxycarbonylamino)-3,3-dimethylbutanoyl)octahydrocyclopenta[c]pyrrole-1-carboxylate
• CAS No.: 926276-15-5
• Molecular Formula: C₂₆H₃₈N₂O₅
• Molecular Weight: 458.598
• Mol file: 926276-15-5.mol

Synonyms:(1S,3aR,6aS)-tert-butyl 2-((S)-2-(benzyloxycarbonylamino)-3,3-dimethylbutanoyl)octahydrocyclopenta[c]pyrrole-1-carboxylate

Chemical Property of (1S,3aR,6aS)-tert-butyl 2-((S)-2-(benzyloxycarbonylamino)-3,3-dimethylbutanoyl)octahydrocyclopenta[c]pyrrole-1-carboxylate

Chemical Property:

• Boiling Point: 592℃
• Flash Point: 312℃
• Density: 1.132

Purity/Quality:

95%-98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,3aR,6aS)-tert-butyl 2-((S)-2-(benzyloxycarbonylamino)-3,3-dimethylbutanoyl)octahydrocyclopenta[c]pyrrole-1-carboxylate

There total 4 articles about (1S,3aR,6aS)-tert-butyl 2-((S)-2-(benzyloxycarbonylamino)-3,3-dimethylbutanoyl)octahydrocyclopenta[c]pyrrole-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:

tert-butyl (1S,3aR,6aS)-octahydrocyclopenta[c]pyrrole-1-carboxylate (714194-68-0) + (S)-2-(((benzyloxy)carbonyl)amino)-3,3-dimethylbutanoic acid dicyclohexylammonium salt (62965-37-1) → (1S,3aR,6aS)-tert-butyl 2-((S)-2-(benzyloxycarbonylamino)-3,3-dimethylbutanoyl)octahydrocyclopenta[c]pyrrole-1-carboxylate (926276-15-5)

Guidance literature:

(S)-2-(((benzyloxy)carbonyl)amino)-3,3-dimethylbutanoic acid dicyclohexylammonium salt; With sulfuric acid; In tert-butyl methyl ether; water; at 20 ℃; for 0.5h;

With 4-methyl-morpholine; In tert-butyl methyl ether;

tert-butyl (1S,3aR,6aS)-octahydrocyclopenta[c]pyrrole-1-carboxylate; With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tert-butyl methyl ether; Isopropyl acetate; water; at 0 - 20 ℃; for 7h; Product distribution / selectivity;

Reference yield:

(S)-2-(((benzyloxy)carbonyl)amino)-3,3-dimethylbutanoic acid dicyclohexylammonium salt (62965-37-1) → (1S,3aR,6aS)-tert-butyl 2-((S)-2-(benzyloxycarbonylamino)-3,3-dimethylbutanoyl)octahydrocyclopenta[c]pyrrole-1-carboxylate (926276-15-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sulfuric acid / water; Isopropyl acetate / 0.5 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

2.2: 20 - 25 °C

With sulfuric acid; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In Isopropyl acetate; water;

Reference yield:

tert-butyl (1S,3aR,6aS)-octahydrocyclopenta[c]pyrrole-1-carboxylate (714194-68-0) + (S)-N-carbobenzoxy-tert-butylleucine (62965-10-0) → (1S,3aR,6aS)-tert-butyl 2-((S)-2-(benzyloxycarbonylamino)-3,3-dimethylbutanoyl)octahydrocyclopenta[c]pyrrole-1-carboxylate (926276-15-5)

Guidance literature:

tert-butyl (1S,3aR,6aS)-octahydrocyclopenta[c]pyrrole-1-carboxylate; (S)-N-carbobenzoxy-tert-butylleucine; With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In Isopropyl acetate; water; N,N-dimethyl-formamide; at 0 - 20 ℃; for 20h;

With 4-methyl-morpholine; histamine dichloride; In Isopropyl acetate; water; N,N-dimethyl-formamide; for 3.5h; Product distribution / selectivity;

upstream raw materials:

tert-butyl (1S,3aR,6aS)-octahydrocyclopenta[c]pyrrole-1-carboxylate

(S)-N-carbobenzoxy-tert-butylleucine

(S)-2-(((benzyloxy)carbonyl)amino)-3,3-dimethylbutanoic acid dicyclohexylammonium salt

tert-butyl (1S,3aR,6aS)-octahydrocyclopenta[c]pyrrole-1-carboxylate oxalic acid salt

Refernces

• 1、 -. "PROCESSES AND INTERMEDIATES". Page/Page column 37. . Retrieved 2012/12/13.