Sodium borohydride → HCID 53640764, compound

HRID 1003609Notes

Reaction equation

HRID 1003609 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-44d8af16ac974090a40b86007c9cf2b8
Source dataset
uspto-grants-2000_04
Patent number
US06046213

Reaction notes

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