(1S,2S,3R)-2-[N-(benzyloxycarbonyl)amino]-3-methylcyclopentanecarboxylic acid

Base Information

Chemical Name:(1S,2S,3R)-2-[N-(benzyloxycarbonyl)amino]-3-methylcyclopentanecarboxylic acid
CAS No.:1280736-82-4
Molecular Formula:C₁₅H₁₉NO₄
Molecular Weight:277.32
Hs Code.:

Synonyms:(1S,2S,3R)-2-[N-(benzyloxycarbonyl)amino]-3-methylcyclopentanecarboxylic acid

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Chemical Property of (1S,2S,3R)-2-[N-(benzyloxycarbonyl)amino]-3-methylcyclopentanecarboxylic acid

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Technology Process of (1S,2S,3R)-2-[N-(benzyloxycarbonyl)amino]-3-methylcyclopentanecarboxylic acid

There total 4 articles about (1S,2S,3R)-2-[N-(benzyloxycarbonyl)amino]-3-methylcyclopentanecarboxylic acid 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: 86.0%

: 1280736-79-9
tert-butyl (1S,2S,3R)-2-[N-(benzyloxycarbonyl)amino]-3-methylcyclopentanecarboxylate

: 1280736-82-4
(1S,2S,3R)-2-[N-(benzyloxycarbonyl)amino]-3-methylcyclopentanecarboxylic acid

Guidance literature:: With trifluoroacetic acid; In dichloromethane; at 0 - 20 ℃; for 3h; chemoselective reaction; Inert atmosphere;
DOI:10.1016/j.tetasy.2010.12.007

Reference yield:

: tert-butyl (αS)-2-[n-benzyl-N-(α-methylbenzyl)-amino]-3-methylcyclopentanecarboxylate

: 1280736-82-4
(1S,2S,3R)-2-[N-(benzyloxycarbonyl)amino]-3-methylcyclopentanecarboxylic acid

Guidance literature:: Multi-step reaction with 4 steps

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

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

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

4: trifluoroacetic acid / dichloromethane / 3 h / 0 - 20 °C / Inert atmosphere

With 20 % Pd(OH)2/C; potassium tert-butylate; hydrogen; triethylamine; trifluoroacetic acid; tert-butyl alcohol; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1016/j.tetasy.2010.12.007

Reference yield:

: 646518-16-3,816444-35-6
tert-butyl (1S,2S,3R)-3-methyl-2-aminocyclopentane-1-carboxylate

: 1280736-82-4
(1S,2S,3R)-2-[N-(benzyloxycarbonyl)amino]-3-methylcyclopentanecarboxylic acid

Guidance literature:: Multi-step reaction with 2 steps

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

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

With triethylamine; trifluoroacetic acid; In tetrahydrofuran; dichloromethane;
DOI:10.1016/j.tetasy.2010.12.007