Ammonia → (1R,3S)-3-(benzylamino)cyclopentanecarboxamide

HRID 1896306Notes

Reaction equation

HRID 1896306 reaction equation
[NH3:1].[CH2:2]([NH:9][C@H:10]1[CH2:14][CH2:13][C@@H:12]([C:15]([O:17]C)=O)[CH2:11]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1>CO>[CH2:2]([NH:9][C@H:10]1[CH2:14][CH2:13][C@@H:12]([C:15]([NH2:1])=[O:17])[CH2:11]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 67382789HCID 67382789, compound

Product 1

HCID 67382732(1R,3S)-3-(benzylamino)cyclopentanecarboxamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Ammonia gas was passed into a solution of (1R,3S)-methyl 3-(benzylamino)cyclopentanecarboxylate (250 mg, 1.14 mmol) in MeOH (5 ml) at −78° C. in a steel bomb. The reaction mixture was slowly warmed to room temperature, heated further to 100° C. and stirred for 24 h. The reaction mixture was concentrated and dried under vacuum to afford 250 mg of (1R,3S)-3-(benzylamino)cyclopentanecarboxamide with 50% purity as brown liquid which was proceeded as crude compound for the next step.

Workup

  1. temperatureheated further to 100° C.
  2. concentrationThe reaction mixture was concentrated
  3. customdried under vacuum

Sources & evidence

ORD record
ord-77295d58d81445e590f7d49fdfa11283
Source dataset
uspto-grants-2013_08
Patent number
US08518948B2

Reaction notes

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