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Water → (2S,3S)-2-(3,5-Bis-trifluoromethyl-benzyloxy)-3-phenyl-morpholine

HRID 862683
Notes
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Reaction equation

HRID 862683 reaction equation
C([N:8]1[CH2:13][CH2:12][O:11][C@H:10]([O:14][CH2:15][C:16]2[CH:21]=[C:20]([C:22]([F:25])([F:24])[F:23])[CH:19]=[C:18]([C:26]([F:29])([F:28])[F:27])[CH:17]=2)[C@@H:9]1[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)C1C=CC=CC=1.O.[H][H]>C(O)C.[Pd]>[F:29][C:26]([F:27])([F:28])[C:18]1[CH:17]=[C:16]([CH:21]=[C:20]([C:22]([F:23])([F:24])[F:25])[CH:19]=1)[CH2:15][O:14][C@H:10]1[O:11][CH2:12][CH2:13][NH:8][C@H:9]1[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 962WaterHCID 107438244-benzyl-2-(S)-(3,5-bis(trifluoromethyl)benzyloxy)-3-(S)-phenylmorpholineHCID 178418361HCID 178418361, compound

Product 1

HCID 9887525(2S,3S)-2-(3,5-Bis-trifluoromethyl-benzyloxy)-3-phenyl-morpholineYield 80%

Reagents, catalysts & solvents 2

HCID 23938Palladium
Catalyst
HCID 702EthanolSolvent

Procedure

A mixture of 0.68 g (1.37 mmole) of 4-benzyl-2-(S)-(3,5-bis(trifluoromethyl)benzyloxy)-3-(S)-phenylmorpholine and 280 mg of 10% Pd/C in 36 mL of 97:3 ethanol:water was stirred under one atmosphere of hydrogen for 15 hr. The mixture was filtered through Celite, the filter cake was washed generously with ethanol, and the filtrated was concentrated in vacuo. The residue was purified by flash chromatography on 68 g of silica eluting with 1 L of 33:67 hexanes:diethyl ether, then 1 L of 25:75 hexanes:diethyl ether to give 0.443 g (80%) of an oil, which by 1H NMR was pure cis morpholine.

Workup

  1. filtrationThe mixture was filtered through Celite
  2. washthe filter cake was washed generously with ethanol
  3. concentrationthe filtrated was concentrated in vacuo
  4. customThe residue was purified by flash chromatography on 68 g of silica eluting with 1 L of 33:67 hexanes

Sources & evidence

ORD record
ord-62ba9d34ce4e4bd5bf78deae92f85de8
Source dataset
uspto-grants-1998_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05719147

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes