HCID 86618167, compound → HCID 68564795, compound

HRID 2246610Notes

Reaction equation

HRID 2246610 reaction equation
[C:1]([NH:4][CH2:5][C@@H:6]1[CH2:11][C@H:10]([O:12][CH3:13])[CH2:9][CH2:8][C@@H:7]1[N:14]1[CH2:18][CH2:17][C@H:16]([NH:19]C(=O)OCC2C=CC=CC=2)[C:15]1=[O:30])(=[O:3])[CH3:2].[H][H]>CO.[Pd]>[NH2:19][C@H:16]1[CH2:17][CH2:18][N:14]([C@H:7]2[CH2:8][CH2:9][C@@H:10]([O:12][CH3:13])[CH2:11][C@H:6]2[CH2:5][NH:4][C:1](=[O:3])[CH3:2])[C:15]1=[O:30]

Participants

5

Reactant 2

HCID 86618167HCID 86618167, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 68564795HCID 68564795, compoundYield 98.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A sample of the benzyl (S)-1-((1S,2S,4R)-2-(acetamidomethyl)-4-methoxycyclohexyl)-2-oxopyrrolidin-3-ylcarbamate (614 mg, 1.471 mmol) and Pd/C (62.6 mg, 0.294 mmol) were stirred in MeOH (30 mL) at room temperature under 50 psi hydrogen atmosphere for 2 h. The suspension was filtered through Celite with EtOAc, concentrated and dried in vacuo to yield N-(((1S,2S,5R)-2-((S)-3-amino-2-oxopyrrolidin-1-yl)-5-methoxycyclohexyl)methyl)acetamide (410 mg, 1.447 mmol, 98% yield) as a white solid. LC/MS found [M+H]+=284.24.

Workup

  1. filtrationThe suspension was filtered through Celite with EtOAc
  2. concentrationconcentrated
  3. customdried in vacuo

Sources & evidence

ORD record
ord-12832e89ab3c4d5a9a021db0183cbc8e
Source dataset
uspto-grants-2010_03
Patent number
US07687508B2

Reaction notes

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