Ammonia → cis-3-(Boc-amino)cyclopentanecarboxamide

HRID 2176947Notes

Reaction equation

HRID 2176947 reaction equation
[NH3:1].C[O:3][C:4]([C@@H:6]1[CH2:10][CH2:9][C@H:8]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[CH2:7]1)=O>CO>[C:4]([C@@H:6]1[CH2:10][CH2:9][C@H:8]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[CH2:7]1)(=[O:3])[NH2:1]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 10466952HCID 10466952, compound

Product 1

HCID 59028693cis-3-(Boc-amino)cyclopentanecarboxamideYield 85.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Ammonia gas was passed into a solution of tert-butyl (1S,3R)-3-(methoxycarbonyl)cyclopentylcarbamate (2.0 g, 8.2 mmol) in MeOH (20 ml) at −78° C. in a steal bomb. The reaction mixture was slowly warmed to room temperature, heated to 80° C. and stirred further for 48 h. The reaction mixture was cooled to room temperature and concentrated to afford 1.6 g (85.5%) of tert-butyl (1S,3R)-3-carbamoylcyclopentylcarbamate as brownish solid.

Workup

  1. temperatureheated to 80° C.
  2. temperatureThe reaction mixture was cooled to room temperature
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-910b08748e5e4b6c819968bad62836ca
Source dataset
uspto-grants-2015_06
Patent number
US09067888B2

Reaction notes

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