Water → HCID 69678038, compound

HRID 1072063Notes

Reaction equation

HRID 1072063 reaction equation
CCC(C)[BH-](C(C)CC)C(C)CC.[Li+].[CH2:15]([O:22][C:23]1[CH:28]=[C:27]([F:29])[CH:26]=[CH:25][C:24]=1[CH:30]=[CH:31][C:32](=[O:43])[C@@H:33]([O:35][Si:36]([C:39]([CH3:42])([CH3:41])[CH3:40])([CH3:38])[CH3:37])[CH3:34])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.O.CCOC(C)=O>C1COCC1>[CH2:15]([O:22][C:23]1[CH:28]=[C:27]([F:29])[CH:26]=[CH:25][C:24]=1[CH:30]=[CH:31][C@H:32]([OH:43])[C@@H:33]([O:35][Si:36]([C:39]([CH3:42])([CH3:41])[CH3:40])([CH3:37])[CH3:38])[CH3:34])[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 3611392Lithium tri-s-butylborohydrideHCID 69678059HCID 69678059, compound

Product 1

HCID 69678038HCID 69678038, compoundYield 66.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-20 °C

Procedure

1M solution of L-selectride in THF (11.5 ml) was added dropwise below −30° C. to a solution of (S)-1-(2-benzyloxy-4-fluorophenyl)-4-tert-butyldimethylsilyloxy-1-penten-3-one (3.94 g) in THF (18 ml). The mixture was stirred at −20° C. for 30 min. Water and EtOAc were added and the organic layer was washed with brine, dried and evaporated. The residue was chromatographed over silica gel (100 g) eluting with a mixture of hexane and EtOAc (30:1) to afford a pale yellow oil of (3S,4S)-1-(2-benzyloxy-4-fluorophenyl)-4-tert-butyldimethylsilyloxy-1-penten-3-ol (2.64 g, 66.7%).

Workup

  1. washthe organic layer was washed with brine
  2. customdried
  3. customevaporated
  4. customThe residue was chromatographed over silica gel (100 g)
  5. washeluting with a mixture of hexane and EtOAc (30:1)

Sources & evidence

ORD record
ord-e19a620fed6b4f4a90ab1b961866074b
Source dataset
uspto-grants-2005_06
Patent number
US06908940B2

Reaction notes

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