tert-butyl (S,S,S)-2-[N-(benzyloxycarbonyl)amino]-3-benzylcyclopentanecarboxylate

Base Information

• Chemical Name: tert-butyl (S,S,S)-2-[N-(benzyloxycarbonyl)amino]-3-benzylcyclopentanecarboxylate
• CAS No.: 1280736-78-8
• Molecular Formula: C₂₅H₃₁NO₄
• Molecular Weight: 409.525
• Mol file: 1280736-78-8.mol

Synonyms:tert-butyl (S,S,S)-2-[N-(benzyloxycarbonyl)amino]-3-benzylcyclopentanecarboxylate

Chemical Property of tert-butyl (S,S,S)-2-[N-(benzyloxycarbonyl)amino]-3-benzylcyclopentanecarboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl (S,S,S)-2-[N-(benzyloxycarbonyl)amino]-3-benzylcyclopentanecarboxylate

There total 3 articles about tert-butyl (S,S,S)-2-[N-(benzyloxycarbonyl)amino]-3-benzylcyclopentanecarboxylate 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: 63.0%

t-butyl (1S,2S,3S)-3-benzyl-2-aminocyclopentane-1-carboxylate (820236-58-6) + benzyl chloroformate (501-53-1,94274-21-2) → tert-butyl (S,S,S)-2-[N-(benzyloxycarbonyl)amino]-3-benzylcyclopentanecarboxylate (1280736-78-8)

Guidance literature:

With triethylamine; In tetrahydrofuran; at 0 - 20 ℃; for 16h; Inert atmosphere;

DOI:10.1016/j.tetasy.2010.12.007

Reference yield:

tert-butyl (1S,2S,3S,αS)-3-benzyl-2-(N-benzyl-N-α-methylbenzylamino)-cyclopentane-1-carboxylate (820236-49-5) → tert-butyl (S,S,S)-2-[N-(benzyloxycarbonyl)amino]-3-benzylcyclopentanecarboxylate (1280736-78-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 20 % Pd(OH)2/C; hydrogen / ethyl acetate / 16 h / 20 °C / 3800.26 Torr

2: triethylamine / tetrahydrofuran / 16 h / 0 - 20 °C / Inert atmosphere

With 20 % Pd(OH)2/C; hydrogen; triethylamine; In tetrahydrofuran; ethyl acetate;

DOI:10.1016/j.tetasy.2010.12.007

Reference yield:

tert-butyl (1R,2S,3S,αS)-3-benzyl-2-(N-benzyl-N-α-methylbenzylamino)-cyclopentane-1-carboxylate (816444-33-4) → tert-butyl (S,S,S)-2-[N-(benzyloxycarbonyl)amino]-3-benzylcyclopentanecarboxylate (1280736-78-8)

Guidance literature:

Multi-step reaction with 3 steps

1: potassium tert-butylate; tert-butyl alcohol / 8 h / Reflux; Inert atmosphere

2: 20 % Pd(OH)2/C; hydrogen / ethyl acetate / 16 h / 20 °C / 3800.26 Torr

3: triethylamine / tetrahydrofuran / 16 h / 0 - 20 °C / Inert atmosphere

With 20 % Pd(OH)2/C; potassium tert-butylate; hydrogen; triethylamine; tert-butyl alcohol; In tetrahydrofuran; ethyl acetate;

DOI:10.1016/j.tetasy.2010.12.007

upstream raw materials:

t-butyl (1S,2S,3S)-3-benzyl-2-aminocyclopentane-1-carboxylate

benzyl chloroformate

tert-butyl (1S,2S,3S,αS)-3-benzyl-2-(N-benzyl-N-α-methylbenzylamino)-cyclopentane-1-carboxylate

tert-butyl (1R,2S,3S,αS)-3-benzyl-2-(N-benzyl-N-α-methylbenzylamino)-cyclopentane-1-carboxylate

Downstream raw materials:

(S,S,S)-2-[N-(benzyloxycarbonyl)amino]-3-benzylcyclopentanecarboxylic acid

C₃₈H₄₆N₂O₅

C₃₀H₄₀N₂O₃

C₃₄H₃₈N₂O₅