Sodium cyanoborohydride → N,N-diethyl-5-phenyl-3,5-dihydroxypentanamide

HRID 2226280

Reaction equation

HRID 2226280 reaction equation
[CH2:1]([N:3]([CH2:18][CH3:19])[C:4](=[O:17])[CH2:5][C:6](=[O:16])[CH2:7][CH:8]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[OH:9])[CH3:2].C([BH3-])#N.[Na+]>CC(C)[O-].CC(C)[O-].CC(C)[O-].[Cl-].[Ti+4]>[CH2:18]([N:3]([CH2:1][CH3:2])[C:4](=[O:17])[CH2:5][CH:6]([OH:16])[CH2:7][CH:8]([C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)[OH:9])[CH3:19]

Participants

4

Reactant 2

HCID 5003444Sodium cyanoborohydrideHCID 18967271N,N-diethyl-5-phenyl-5-hydroxy-3-oxopentanamide

Product 1

HCID 19003821N,N-diethyl-5-phenyl-3,5-dihydroxypentanamideYield 70.2%

Reagents, catalysts & solvents 1

HCID 3084342Chlorotitanium triisopropoxideCatalyst

Procedure

By carrying out the reaction as in Example 9 but starting from 1.02 g of N,N-diethyl-5-phenyl-5-hydroxy-3-oxopentanamide (3.92 mmol), 1.05 cm3 of titanium chloride triisopropoxide (4.18 mmol) and from 283.9 mg of sodium cyanoborohydride (4.28 mmol), there is obtained, with a yield of 70.2%, 730 mg of N,N-diethyl-5-phenyl-3,5-dihydroxypentanamide for which the syn/anti ratio is equal to 80/20.

Workup

  1. customthe reaction as in Example 9

Sources & evidence

ORD record
ord-a279125cc388433fadb42102b4837784
Source dataset
uspto-grants-1994_09
Patent number
US05347039

Linked notes

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