Sodium borohydride → HCID 53640764, compound

HRID 1384304Notes

Reaction equation

HRID 1384304 reaction equation
[BH4-].[Na+].[CH3:3][C:4]1[CH:5]=[C:6]([C:22](=[O:42])[CH:23]([N:25]2[CH2:30][CH2:29][C:28]([C:32]3[CH:37]=[CH:36][C:35]([C:38]([F:41])([F:40])[F:39])=[CH:34][CH:33]=3)([OH:31])[CH2:27][CH2:26]2)[CH3:24])[CH:7]=[C:8]([CH3:21])[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>[CH3:3][C:4]1[CH:5]=[C:6]([C@@H:22]([OH:42])[C@H:23]([N:25]2[CH2:26][CH2:27][C:28]([C:32]3[CH:37]=[CH:36][C:35]([C:38]([F:41])([F:40])[F:39])=[CH:34][CH:33]=3)([OH:31])[CH2:29][CH2:30]2)[CH3:24])[CH:7]=[C:8]([CH3:21])[C:9]=1[O:10][Si:11]([CH:18]([CH3:19])[CH3:20])([CH:15]([CH3:16])[CH3:17])[CH:12]([CH3:13])[CH3:14]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 21186660HCID 21186660, compound

Product 1

HCID 53640764HCID 53640764, compoundYield 31.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of sodium borohydride (0.090 g, 2.38 mmol) and ethanol (5 mL) was stirred 10 min and then 1-(3,5-dimethyl-4-triisopropylsilyloxyphenyl)-2-(4-(4-trifluoromethylphenyl)-4-hydroxypiperidin-1-yl)-propan-1-one (1.30 g, 2.25 mmol in 25 mL of ethanol) was added. The reaction was stirred at ambient temperature overnight. The white solid which precipitated was collected by filtration and dried to yield 0.408 g (31%) of (1R*,2R*)-1-(3,5-dimethyl-4-triisopropylsilyloxyphenyl)-2-(4-(4-trifluoromethylphenyl)-4-hydroxypiperidin-1-yl)-propan-1-ol which was suitable for use without further purification and had: mp 177-177.5° C. Analysis calculated for C32H48F3NO3Si.0.25 H2O: C, 65.78; H, 8.37; N, 2.40. Found: C, 65.65; H, 8.51; N, 2.57.

Workup

  1. stirringThe reaction was stirred at ambient temperature overnight
  2. customThe white solid which precipitated
  3. filtrationwas collected by filtration
  4. customdried

Sources & evidence

ORD record
ord-2c1ce455dda348e19f70c4457dd65763
Source dataset
uspto-grants-2001_07
Patent number
US06258827B1

Reaction notes

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