methyl (3aR,5R,6aR)-2-benzyl-5-((tert-butoxycarbonyl)amino)octahydrocyclopenta[c]pyrrole-3a-carboxylate

Base Information

• Chemical Name: methyl (3aR,5R,6aR)-2-benzyl-5-((tert-butoxycarbonyl)amino)octahydrocyclopenta[c]pyrrole-3a-carboxylate
• CAS No.: 1443232-24-3
• Molecular Formula: C₂₁H₃₀N₂O₄
• Molecular Weight: 374.48
• Mol file: 1443232-24-3.mol

Synonyms:methyl (3aR,5R,6aR)-2-benzyl-5-((tert-butoxycarbonyl)amino)octahydrocyclopenta[c]pyrrole-3a-carboxylate

Chemical Property of methyl (3aR,5R,6aR)-2-benzyl-5-((tert-butoxycarbonyl)amino)octahydrocyclopenta[c]pyrrole-3a-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (3aR,5R,6aR)-2-benzyl-5-((tert-butoxycarbonyl)amino)octahydrocyclopenta[c]pyrrole-3a-carboxylate

There total 1 articles about methyl (3aR,5R,6aR)-2-benzyl-5-((tert-butoxycarbonyl)amino)octahydrocyclopenta[c]pyrrole-3a-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: 80.0%

N-benzyl-N-(methoxymethyl)-N-[(trimethylsilyl)methyl]amine (93102-05-7) + methyl (4R)-4-[(tert-butyloxycarbonyl)amino]cyclopent-1-ene-1-carboxylate (251327-01-2) → methyl (3aR,5R,6aR)-2-benzyl-5-((tert-butoxycarbonyl)amino)octahydrocyclopenta[c]pyrrole-3a-carboxylate (1443232-24-3)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 2 ℃; for 2h; diastereoselective reaction; Inert atmosphere;

DOI:10.1016/j.tetasy.2013.04.014

Reference yield: 75.0%

methyl (3aR,5R,6aR)-2-benzyl-5-((tert-butoxycarbonyl)amino)octahydrocyclopenta[c]pyrrole-3a-carboxylate (1443232-24-3) + (2E)-but-2-enedioic acid (110-17-8,26099-09-2) → (3aR,5R,6aR)-methyl 2-benzyl-5-(tert-butoxycarbonylamino)octahydrocyclopenta[c]pyrrole-3a-carboxylate fumarate (1443232-25-4)

Guidance literature:

In acetone; at 20 - 50 ℃; Inert atmosphere;

DOI:10.1016/j.tetasy.2013.04.014

Reference yield:

methyl (3aR,5R,6aR)-2-benzyl-5-((tert-butoxycarbonyl)amino)octahydrocyclopenta[c]pyrrole-3a-carboxylate (1443232-24-3) → (3aR,5R,6aR)-2-benzyl 3a-methyl 5-((tert-butoxycarbonyl)amino)hexahydrocyclopenta[c]pyrrole-2,3a(1H)-dicarboxylate (1537880-01-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 5% Pd(OH)2/C; hydrogen / methanol / 2585.81 Torr

2: triethylamine / dichloromethane / 3 h / 0 - 20 °C / Inert atmosphere

With 5% Pd(OH)2/C; hydrogen; triethylamine; In methanol; dichloromethane;

upstream raw materials:

N-benzyl-N-(methoxymethyl)-N-[(trimethylsilyl)methyl]amine

methyl (4R)-4-[(tert-butyloxycarbonyl)amino]cyclopent-1-ene-1-carboxylate

Downstream raw materials:

(3aR,5R,6aR)-methyl 2-benzyl-5-(tert-butoxycarbonylamino)octahydrocyclopenta[c]pyrrole-3a-carboxylate fumarate

tert-butyl ((3aR,5R,6aR)-2-cinnamoyl-3a-(3-(trifluoromethyl)-5,6,7,8-tetrahydro-1,6-naphthyridine-6-carbonyl)octahydrocyclopenta[c]pyrrol-5-yl)carbamate

tert-butyl ((3aR,5R,6aR)-2-phenyl-3a-(3-(trifluoromethyl)-5,6,7,8-tetrahydro-1,6-naphthyridine-6-carbonyl)octahydrocyclopenta[c]pyrrol-5-yl)carbamate

(3aR,5R,6aR)-2-benzyl 3a-methyl 5-((tert-butoxycarbonyl)amino)hexahydrocyclopenta[c]pyrrole-2,3a(1H)-dicarboxylate