HCID 69678038, compound → HCID 69677833, compound

HRID 1072064Notes

Reaction equation

HRID 1072064 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([F:15])[CH:12]=[CH:11][C:10]=1[CH:16]=[CH:17][C@H:18]([OH:29])[C@@H:19]([O:21][Si:22]([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23])[CH3:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CCOC(C)=O.[Pd]>[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([F:15])[CH:12]=[CH:11][C:10]=1[CH2:16][CH2:17][C@H:18]([OH:29])[C@@H:19]([O:21][Si:22]([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:23])[CH3:24])[CH3:20])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1.[OH:8][C:9]1[CH:14]=[C:13]([F:15])[CH:12]=[CH:11][C:10]=1[CH2:16][CH2:17][C@H:18]([OH:29])[C@@H:19]([O:21][Si:22]([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:23])[CH3:24])[CH3:20]

Participants

5

Reactant 1

HCID 69678038HCID 69678038, compound

Product 2

HCID 69677833HCID 69677833, compoundYield 51.3%HCID 69678558HCID 69678558, compoundYield 45.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of (3S,4S)-1-(2-benzyloxy-4-fluorophenyl)-4-tert-butyldimethylsilyloxy-1-penten-3-ol (2.62 g) and 10% Pd—C (0.52 g) in EtOAc (65 ml) was stirred under hydrogen atmosphere at atmospheric pressure for 13 min. Pd—C was removed by filtration and the filtrate was evaporated. The residual oil (2.38 g) was chromatographed over silica gel (30 g) eluting with a mixture of hexane and EtOAc (50:1 to 2:1) to give a colorless oil of (3S,4S)-1-(2-benzyloxy-4-fluorophenyl)-4-tert-butyldimethylsilyloxy-3-pentanol (1.35 g, 51.3%) and (3S,4S)-1-(2-hydroxy-4-fluorophenyl)-4-tert-butyldimethylsilyloxy-3-pentanol (0.94 g, 45.5%).

Workup

  1. customPd—C was removed by filtration
  2. customthe filtrate was evaporated
  3. customThe residual oil (2.38 g) was chromatographed over silica gel (30 g)
  4. washeluting with a mixture of hexane and EtOAc (50:1 to 2:1)

Sources & evidence

ORD record
ord-70bb84863613424994efe1a9f801e6e9
Source dataset
uspto-grants-2005_06
Patent number
US06908940B2

Reaction notes

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