Sodium borohydride → MDL 11,939

HRID 440372Notes

Reaction equation

HRID 440372 reaction equation
[C:1]1([C:7]([CH:9]2[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:11][CH2:10]2)=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[BH4-].[Na+]>O1CCCC1.[OH-].[Na+]>[C:1]1([CH:7]([CH:9]2[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:11][CH2:10]2)[OH:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 10379653HCID 10379653, compound

Product 1

HCID 71781MDL 11,939

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of phenyl-[1-(2-phenylethyl)-4-piperidyl]-ketone (0.10 g) in tetrahydrofuran (0.40 g) was added to wet surface-modified adsorbent of Example 10 (1.0 g) in excess aqueous NaOH pH 9.0 (2.0 mL). This mixture was stirred at ambient temperature for 30 minutes. After this, NaBH4 (20 mg) was added and the resulting mixture was stirred at ambient temperature for 16 hours. The liquid phase was then decanted and the adsorbent was washed with tetrahydrofuran in order to quantitatively extract all product from the resin. The tetrahydrofuran washings were combined with liquid phase and analyzed by chiral High Pressure Liquid Chromatography (HPLC) using a Chiracel OD-R column commercially available from Chiral Technologist Incorporation and 1.0M aqueous NaClO4 /acetonitrile (60/40 by volume) as a mobile phase. The product α-phenyl-[1-(2-phenylethyl )]-4-piperidinemethanol of a moderate enantiomeric purity (enantiomeric excess of S (-)=25 percent) was obtained.

Workup

  1. stirringthe resulting mixture was stirred at ambient temperature for 16 hours
  2. customThe liquid phase was then decanted
  3. washthe adsorbent was washed with tetrahydrofuran in order
  4. extractionto quantitatively extract all product from the resin

Sources & evidence

ORD record
ord-abbf93daf3a84538ae383159046a9eb0
Source dataset
uspto-grants-1996_05
Patent number
US05519064

Reaction notes

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