(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 16390Notes

Reaction equation

HRID 16390 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>C(O)C.[C].[Pd]>[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 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

A suspension of (3R,5R)-3-acetyl-5-(3,4,5-trifluorophenyl)morpholine-4-carboxylic acid benzyl ester (800 mg) and 10% palladium-carbon (79.2 mg, 50% water content) in ethanol (15 mL) was stirred under a hydrogen atmosphere for 15 minutes. The catalyst was filtered off over Celite. The obtained filtrate was concentrated, to thereby obtain the titled compound (529 mg). The physical properties of the compound were as follows.

Workup

  1. filtrationThe catalyst was filtered off over Celite
  2. concentrationThe obtained filtrate was concentrated

Sources & evidence

ORD record
ord-c5ddc4150cdf4cbc8669a1f35b2efa29
Source dataset
uspto-grants-2010_06
Patent number
US07737141B2

Reaction notes

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