Sodium borohydride → HCID 15453440, compound

HRID 1384299Notes

Reaction equation

HRID 1384299 reaction equation
[BH4-].[Na+].[F:3][C:4]1[CH:5]=[C:6]([C:21](=[O:38])[CH:22]([N:24]2[CH2:29][CH2:28][C:27]([C:31]3[CH:36]=[CH:35][C:34]([F:37])=[CH:33][CH:32]=3)([OH:30])[CH2:26][CH2:25]2)[CH3:23])[CH:7]=[CH:8][C:9]=1[O:10][Si:11]([CH:18]([CH3:20])[CH3:19])([CH:15]([CH3:17])[CH3:16])[CH:12]([CH3:14])[CH3:13]>C(O)C>[F:3][C:4]1[CH:5]=[C:6]([CH:21]([OH:38])[CH:22]([N:24]2[CH2:25][CH2:26][C:27]([C:31]3[CH:32]=[CH:33][C:34]([F:37])=[CH:35][CH:36]=3)([OH:30])[CH2:28][CH2:29]2)[CH3:23])[CH:7]=[CH:8][C:9]=1[O:10][Si:11]([CH:12]([CH3:13])[CH3:14])([CH:15]([CH3:17])[CH3:16])[CH:18]([CH3:20])[CH3:19]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 15453439HCID 15453439, compound

Product 1

HCID 15453440HCID 15453440, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of sodium borohydride (0.027 g, 0.717 mmol) and ethanol (10 mL) was stirred 10 min and then 1-(3-fluoro-4-triisopropylsilyloxyphenyl)-2-(4-(4-fluorophenyl)-4-hydroxypiperidin-1-yl)-propan-1-one (0.371 g, 0.717 mmol in 10 mL of ethanol) was added. The reaction was stirred at ambient temperature overnight. The mixture was concentrated and the residue was partitioned between ethyl acetate and water. The phases were separated and the organic phase was washed with brine, dried over calcium sulfate and concentrated. The residue was flash chromatographed on silica gel (0.75×3 inches packed in hexane) with elution proceeding as follows: 10% ethyl acetate/hexane (200 mL), nil; 10% ethyl acetate/hexane (100 mL) and 20% ethyl acetate/hexane (200 mL), to give 0.22 g (59%) of (1R*, 2R*)-1-(3-fluoro-4-triisopropylsilyloxyphenyl)-2-(4-(4-fluorophenyl)-4-hydroxypiperidin-1-yl)-propan-1-ol. A sample recrystallized from ether had: mp 159-160° C.

Workup

  1. stirringThe reaction was stirred at ambient temperature overnight
  2. concentrationThe mixture was concentrated
  3. customthe residue was partitioned between ethyl acetate and water
  4. customThe phases were separated
  5. washthe organic phase was washed with brine
  6. dry with materialdried over calcium sulfate
  7. concentrationconcentrated
  8. customchromatographed on silica gel (0.75×3 inches packed in hexane) with elution proceeding

Sources & evidence

ORD record
ord-dae04e8dedf345ee91b564119e29867b
Source dataset
uspto-grants-2001_07
Patent number
US06258827B1

Reaction notes

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