{4-[(S)-3-((S)-2-Methyl-pyrrolidin-1-yl)-cyclopentyl]-phenyl}-carbamic acid benzyl ester → 4-[(S)-3-((S)-2-Methyl-pyrrolidin-1-yl)-cyclopentyl]-phenylamine

HRID 1027404Notes

Reaction equation

HRID 1027404 reaction equation
C(OC(=O)[NH:10][C:11]1[CH:16]=[CH:15][C:14]([C@H:17]2[CH2:21][CH2:20][CH:19]([N:22]3[CH2:26][CH2:25][CH2:24][C@@H:23]3[CH3:27])[CH2:18]2)=[CH:13][CH:12]=1)C1C=CC=CC=1>CO>[CH3:27][C@H:23]1[CH2:24][CH2:25][CH2:26][N:22]1[CH:19]1[CH2:20][CH2:21][C@H:17]([C:14]2[CH:15]=[CH:16][C:11]([NH2:10])=[CH:12][CH:13]=2)[CH2:18]1

Participants

3

Reactant 1

HCID 67479269{4-[(S)-3-((S)-2-Methyl-pyrrolidin-1-yl)-cyclopentyl]-phenyl}-carbamic acid benzyl ester

Product 1

HCID 674791474-[(S)-3-((S)-2-Methyl-pyrrolidin-1-yl)-cyclopentyl]-phenylamineYield 102.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

{4-[(S)-3-((S)-2-Methyl-pyrrolidin-1-yl)-cyclopentyl]-phenyl}-carbamic acid benzyl ester (0.41 g, 1.08 mmol) was dissolved in MeOH (20 mL) to form a clear solution. The flask was flushed with nitrogen and Pd—C (10%) (50 mg) was added. The solution was stirred under H2 atmosphere at rt for 4 h. TLC (5% of 7N ammonia methanolic solution in DCM) indicated that the reaction was complete. The solution was filtered through a Celite pad, rinsed with MeOH. The filtrate was concentrated in vacuo to obtain 0.27 g (100% yield) of the title compound as an oil.

Workup

  1. customto form a clear solution
  2. customThe flask was flushed with nitrogen and Pd—C (10%) (50 mg)
  3. additionwas added
  4. filtrationThe solution was filtered through a Celite pad
  5. washrinsed with MeOH
  6. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-f514e90923274ab5ba847a03e5297c8b
Source dataset
uspto-grants-2014_05
Patent number
US08735385B2

Reaction notes

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