Sodium borohydride → HCID 70236260, compound

HRID 1003607Notes

Reaction equation

HRID 1003607 reaction equation
[BH4-].[Na+].[CH3:3][C:4]1[CH:5]=[C:6]([C:22](=[O:39])[CH:23]([N:25]2[CH2:30][CH2:29][C:28]([C:32]3[CH:37]=[CH:36][C:35]([Cl:38])=[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:39])[C@H:23]([N:25]2[CH2:30][CH2:29][C:28]([C:32]3[CH:37]=[CH:36][C:35]([Cl:38])=[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:15]([CH3:16])[CH3:17])([CH:12]([CH3:13])[CH3:14])[CH:18]([CH3:19])[CH3:20]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 21186591HCID 21186591, compound

Product 1

HCID 70236260HCID 70236260, compoundYield 56.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of sodium borohydride (0.054 g, 1.43 mmol) and ethanol (5 mL) was stirred 10 min and then 1-(3,5-dimethyl-4-triisopropylsilyloxyphenyl)-2-(4-(4-chlorophenyl)-4-hydroxypiperidin-1-yl)-propan-1-one (0.77 g, 1.42 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 0.44 g (56%) of (1R*,2R*)-1-(3,5-dimethy-4-triisopropylsilyloxyphenyl)-2-(4-(4-chlorophenyl)-4-hydroxypiperdin-1-yl)-propan-1-ol which was suitable for use without further purification and had: mp 211.5-212.5° C.

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-205f6e19249b437d9c708ec9f7dcb661
Source dataset
uspto-grants-2000_04
Patent number
US06046213

Reaction notes

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