HCID 69103087, compound → HCID 11236178, compound

HRID 2250816Notes

Reaction equation

HRID 2250816 reaction equation
[Si:1]([O:8][C@@H:9]([CH3:30])[C@@H:10]([OH:29])[CH:11]=[CH:12][C:13]1[C:18]2[N:19]=[C:20]([C:22]3[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=3)[O:21][C:17]=2[CH:16]=[CH:15][CH:14]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]>CCOC(C)=O.[Pd]>[Si:1]([O:8][C@@H:9]([CH3:30])[C@@H:10]([OH:29])[CH2:11][CH2:12][C:13]1[C:18]2[N:19]=[C:20]([C:22]3[CH:23]=[CH:24][C:25]([Cl:28])=[CH:26][CH:27]=3)[O:21][C:17]=2[CH:16]=[CH:15][CH:14]=1)([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 69103087HCID 69103087, compound

Product 1

HCID 11236178HCID 11236178, compoundYield 103.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of (3S,4S)-4-(tert-butyldimethylsilyloxy)-1-[2-(4-chlorophenyl)-4-benzoxazolyl]-1-penten-3-ol (P0005; 385 mg) and 10% Pd—C (77 mg) in EtOAc (19 ml) was stirred under hydrogen atmosphere at atmospheric pressure for 20 min. Pd—C was removed by filtration and the filtrate was evaporated to give a colorless oil of (3S,4S)-4-(tert-butyldimethylsilyloxy)-1-[2-(4-chlorophenyl)4-benzoxazolyl]pentan-3-ol (P0006; 0.40 g).

Workup

  1. customPd—C was removed by filtration
  2. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-ed50a54046a845cdb157ff17e7adaa49
Source dataset
uspto-grants-2008_01
Patent number
US07317107B2

Reaction notes

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