(R)-2-(4,5-diphenyloxazol-2-yl)-1-trimethylsilyloxy-1-[3-(tertbutyldiphenylsiloxy)benzyl]-2-cyclohexene → (1R, 2S)-2-(4,5-diphenyloxazol-2-yl)-1-trimethylsilyoxy-1-[3-(tertbutyldiphenylsiloxy)benzyl]cyclohexane

HRID 379315Notes

Reaction equation

HRID 379315 reaction equation
[C:1]1([C:7]2[N:8]=[C:9]([C:18]3[C@:19]([O:49][Si:50]([CH3:53])([CH3:52])[CH3:51])([CH2:24][C:25]4[CH:30]=[CH:29][CH:28]=[C:27]([O:31][Si:32]([C:45]([CH3:48])([CH3:47])[CH3:46])([C:39]5[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=5)[C:33]5[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=5)[CH:26]=4)[CH2:20][CH2:21][CH2:22][CH:23]=3)[O:10][C:11]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>CO.CCOC(C)=O.[Pd]>[C:1]1([C:7]2[N:8]=[C:9]([C@H:18]3[CH2:23][CH2:22][CH2:21][CH2:20][C@@:19]3([O:49][Si:50]([CH3:53])([CH3:52])[CH3:51])[CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[C:27]([O:31][Si:32]([C:45]([CH3:48])([CH3:46])[CH3:47])([C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=4)[C:39]4[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=4)[CH:26]=3)[O:10][C:11]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 1

HCID 15550206(R)-2-(4,5-diphenyloxazol-2-yl)-1-trimethylsilyloxy-1-[3-(tertbutyldiphenylsiloxy)benzyl]-2-cyclohexene

Product 1

HCID 131722877(1R, 2S)-2-(4,5-diphenyloxazol-2-yl)-1-trimethylsilyoxy-1-[3-(tertbutyldiphenylsiloxy)benzyl]cyclohexaneYield 87.3%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of (R)-2-(4,5-diphenyloxazol-2-yl)-1-trimethylsilyloxy-1-[3-(tertbutyldiphenylsiloxy)benzyl]-2-cyclohexene (24 g) and 10% Pd/C (10 g) in a mixture of MeOH (200 ml) and EtOAc (500 ml) was stirred under H2 for 8 hours. The catalyst was filtered off and the filtrate was evaporated in vacuo. The residue was purified by chromatography on silica gel to give (1R, 2S)-2-(4,5-diphenyloxazol-2-yl)-1-trimethylsilyoxy-1-[3-(tertbutyldiphenylsiloxy)benzyl]cyclohexane (21 g).

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe filtrate was evaporated in vacuo
  3. customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-a1f91fcb5b974f9493f210b9a32f6d2c
Source dataset
uspto-grants-2001_10
Patent number
US06297267B1

Reaction notes

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