HCID 68767116, compound → HCID 68768096, compound

HRID 1374353Notes

Reaction equation

HRID 1374353 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]([C:25]([CH3:28])([CH3:27])[CH3:26])[CH3:24])[CH2:19][C@H:18]2[C:29]([O:31][CH3:32])=[O:30])[C:13]1=[O:33])=O)C1C=CC=CC=1>CO.[Pd]>[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]([C:25]([CH3:28])([CH3:27])[CH3:26])[CH3:24])[CH2:19][C@H:18]2[C:29]([O:31][CH3:32])=[O:30])[C:13]1=[O:33]

Participants

4

Reactant 1

HCID 68767116HCID 68767116, compound

Product 1

HCID 68768096HCID 68768096, compoundYield 94.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of (1R,2S,5R)-methyl 2-((S)-3-(benzyloxycarbonylamino)-2-oxopyrrolidin-1-yl)-5-(tert-butyl(methyl)amino)cyclohexanecarboxylate (330 mg, 0.65 mmol) in methanol was treated with 100 mg of 10% Pd/C and hydrogenated at 55 psi of H2 in a Parr shaker overnight. The catalyst was filtered and the filtrate concentrated in vacuo to give 200 mg of (1R,2S,5R)-methyl 2-((S)-3-amino-2-oxopyrrolidin-1-yl)-5-(tert-butyl(methyl)amino)-cyclohexanecarboxylate as a white solid. This was used without further purification. MS found: (M+H)+=326.50

Workup

  1. filtrationThe catalyst was filtered
  2. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-bd9c42ee0e864d6cb737045bb68e6f6d
Source dataset
uspto-grants-2007_01
Patent number
US07163937B2

Reaction notes

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