morpholin-4-yl-{4-[(2S)-4-((1R)-1-phenylethyl)-morpholin-2-yl]-phenyl}-methanone → morpholin-4-yl-((2S)-4-morpholin-2-yl-phenyl)-methanone

HRID 1091387Notes

Reaction equation

HRID 1091387 reaction equation
[N:1]1([C:7]([C:9]2[CH:14]=[CH:13][C:12]([C@@H:15]3[O:20][CH2:19][CH2:18][N:17]([C@@H](C4C=CC=CC=4)C)[CH2:16]3)=[CH:11][CH:10]=2)=[O:8])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1>C(O)C.[OH-].[OH-].[Pd+2]>[N:1]1([C:7]([C:9]2[CH:14]=[CH:13][C:12]([C@@H:15]3[O:20][CH2:19][CH2:18][NH:17][CH2:16]3)=[CH:11][CH:10]=2)=[O:8])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1

Participants

4

Reactant 1

HCID 66594396morpholin-4-yl-{4-[(2S)-4-((1R)-1-phenylethyl)-morpholin-2-yl]-phenyl}-methanone

Product 1

HCID 66594327morpholin-4-yl-((2S)-4-morpholin-2-yl-phenyl)-methanoneYield 100%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

A solution of morpholin-4-yl-{4-[(2S)-4-((1R)-1-phenylethyl)-morpholin-2-yl]-phenyl}-methanone (465 mg, 1.20 mmol) and 20% palladium hydroxide on carbon (0.50 g) in ethanol (6.0 ml) was stirred under hydrogen atmosphere at room temperature for 10 hours. The mixture was passed through Celite column and the organic layer was concentrated under reduced pressure to yield morpholin-4-yl-((2S)-4-morpholin-2-yl-phenyl)-methanone (331 mg, 100%) as a clear oil.

Workup

  1. concentrationthe organic layer was concentrated under reduced pressure

Sources & evidence

ORD record
ord-6340d64a582341f3b3c55e7b98832660
Source dataset
uspto-grants-2012_03
Patent number
US08129377B2

Reaction notes

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