HCID 86596905, compound → HCID 68768989, compound

HRID 1171592Notes

Reaction equation

HRID 1171592 reaction equation
[CH:1]([O:4][C@@H:5]1[CH2:10][CH2:9][C@H:8]([N:11]2[CH2:15][CH2:14][C@H:13]([NH:16]C(=O)OCC3C=CC=CC=3)[C:12]2=[O:27])[C@H:7]([CH2:28][S:29]([CH:32]([CH3:34])[CH3:33])(=[O:31])=[O:30])[CH2:6]1)([CH3:3])[CH3:2].[H][H]>CO.[Pd]>[NH2:16][C@H:13]1[CH2:14][CH2:15][N:11]([C@H:8]2[CH2:9][CH2:10][C@@H:5]([O:4][CH:1]([CH3:3])[CH3:2])[CH2:6][C@H:7]2[CH2:28][S:29]([CH:32]([CH3:34])[CH3:33])(=[O:31])=[O:30])[C:12]1=[O:27]

Participants

5

Reactant 2

HCID 86596905HCID 86596905, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 68768989HCID 68768989, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A sample of benzyl (S)-1-((1S,2R,4R)-4-isopropoxy-2-(isopropylsulfonylmethyl)cyclohexyl)-2-oxopyrrolidin-3-ylcarbamate A (faster isomer, 0.41 g) and Pd/C (0.08 g) were taken in MeOH (20 mL) and stirred at rt under 50 psi hydrogen pressure. After stirring overnight, the reaction mixture was filtered through Celite using EtOAc. Upon concentration and drying in vacuo, (S)-3-amino-1-((1S,2R,4R)-4-isopropoxy-2-(isopropylsulfonylmethyl)cyclohexyl)pyrrolidin-2-one was obtained as a clear viscous oil.

Workup

  1. filtrationthe reaction mixture was filtered through Celite
  2. concentrationUpon concentration
  3. customdrying in vacuo

Sources & evidence

ORD record
ord-8a5b86c537c94c69b811fbfcfa873a17
Source dataset
uspto-grants-2010_11
Patent number
US07829571B2

Reaction notes

Loading…