(3R,5R)-3-acetyl-5-(3,4,5-trifluorophenyl)morpholine-4-carboxylic acid benzyl ester → 1-[(3R,5R)-5-(3,4,5-trifluorophenyl)morpholin-3-yl]ethanone

HRID 1677092Notes

Reaction equation

HRID 1677092 reaction equation
C(OC([N:11]1[C@H:16]([C:17]2[CH:22]=[C:21]([F:23])[C:20]([F:24])=[C:19]([F:25])[CH:18]=2)[CH2:15][O:14][CH2:13][C@@H:12]1[C:26](=[O:28])[CH3:27])=O)C1C=CC=CC=1>[Pd].C(O)C>[F:23][C:21]1[CH:22]=[C:17]([C@H:16]2[NH:11][C@@H:12]([C:26](=[O:28])[CH3:27])[CH2:13][O:14][CH2:15]2)[CH:18]=[C:19]([F:25])[C:20]=1[F:24]

Participants

4

Reactant 1

HCID 67372176(3R,5R)-3-acetyl-5-(3,4,5-trifluorophenyl)morpholine-4-carboxylic acid benzyl ester

Product 1

HCID 673707471-[(3R,5R)-5-(3,4,5-trifluorophenyl)morpholin-3-yl]ethanoneYield 100.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

An ethanol (15 mL) suspension of 10% palladium on carbon (50% water contain, 79.2 mg) and (3R,5R)-3-acetyl-5-(3,4,5-trifluorophenyl)morpholin-4-carboxylic acid benzyl ester (800 mg) was stirred for 15 minutes under a hydrogen atmosphere. The catalyst was separated by filtration on celite. The filtrate was concentrated, and the title compound (529 mg) was obtained. The physical property values are as follows.

Workup

  1. customThe catalyst was separated by filtration on celite
  2. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-71b871b6d44d42a2b1c37712270cecc1
Source dataset
uspto-grants-2011_08
Patent number
US08008293B2

Reaction notes

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