Hexane → HCID 9794928, compound

HRID 1953047Notes

Reaction equation

HRID 1953047 reaction equation
C([O:8][NH:9][C:10]([C@H:12]1[CH2:16][C@@H:15]([C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=2)[C:14](=[O:25])[NH:13]1)=[O:11])C1C=CC=CC=1.C(OCC)(=O)C.CCCCCC>CO.[Pd]>[OH:8][NH:9][C:10]([C@H:12]1[CH2:16][C@@H:15]([C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=2)[C:14](=[O:25])[NH:13]1)=[O:11]

Participants

6

Reactant 3

HCID 8058HexaneHCID 8857Ethyl AcetateHCID 15895102HCID 15895102, compound

Product 1

HCID 9794928HCID 9794928, compoundYield 96.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of (2R, 4S)-4-(4-methoxyphenyl)-5-oxopyrrolidine-2-carboxylic acid benzyloxyamide (150 mg, 0.44 mmol) in methanol (15 mL) was treated with 5% palladium on barium sulfate (40 mg) and hydrogenated in a Parr™ shaker at 3 atmospheres pressure for 2.5 hours. The catalyst was removed by filtration and the solvent was evaporated to provide a solid. The title compound (106 mg, 96%) was isolated by crystallization from a mixture of ethyl acetate and hexane.

Workup

  1. customThe catalyst was removed by filtration
  2. customthe solvent was evaporated
  3. customto provide a solid

Sources & evidence

ORD record
ord-7b4d1800c0684fedad8d942cb13b656e
Source dataset
uspto-grants-2000_09
Patent number
US06114361

Reaction notes

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