HCID 68769010, compound → HCID 68768950, compound

HRID 1171541Notes

Reaction equation

HRID 1171541 reaction equation
C(OC([NH:11][C@H:12]1[CH2:16][CH2:15][N:14]([C@H:17]2[CH2:22][CH2:21][C@@H:20]([N:23]([CH:25]([CH3:27])[CH3:26])[CH3:24])[CH2:19][C@H:18]2[CH3:28])[C:13]1=[O:29])=O)C1C=CC=CC=1>CO.[OH-].[OH-].[Pd+2]>[NH2:11][C@H:12]1[CH2:16][CH2:15][N:14]([C@H:17]2[CH2:22][CH2:21][C@@H:20]([N:23]([CH:25]([CH3:26])[CH3:27])[CH3:24])[CH2:19][C@H:18]2[CH3:28])[C:13]1=[O:29]

Participants

4

Reactant 1

HCID 68769010HCID 68769010, compound

Product 1

HCID 68768950HCID 68768950, compoundYield 95.8%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

(S)-3-Benzyloxycarbonylamino-1-((1S,2R,4R)-4-(isopropyl(methyl)amino)-2-methylcyclohexyl)pyrrolidin-2-one (47 mg) in MeOH (5 mL) was charged with 20% Pd(OH)2 (70 mg). The reaction flask was evacuated and then back-filled with hydrogen; this was repeated three more times. The reaction was stirred under 1 atm of H2 for 4 h and then filtered and concentrated to provide (S)-3-amino-1-((1S,2R,4R)-4-(isopropyl(methyl)amino)-2-methylcyclohexyl)pyrrolidin-2-one (30 mg). MS (ES+)=268.3 (M+H)+.

Workup

  1. customThe reaction flask was evacuated
  2. additionback-filled with hydrogen
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-73bdf20921154a138f873431b0d04944
Source dataset
uspto-grants-2010_11
Patent number
US07829571B2

Reaction notes

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