Sodium cyanoborohydride → N,N-diethyl-7-phenyl-3,5-dihydroxy-6-heptenamide

HRID 2226282Notes

Reaction equation

HRID 2226282 reaction equation
[CH2:1]([N:3]([CH2:20][CH3:21])[C:4](=[O:19])[CH2:5][C:6](=[O:18])[CH2:7][CH:8]([OH:17])[CH:9]=[CH:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH3:2].C([BH3-])#N.[Na+]>CC(C)[O-].CC(C)[O-].CC(C)[O-].[Cl-].[Ti+4]>[CH2:20]([N:3]([CH2:1][CH3:2])[C:4](=[O:19])[CH2:5][CH:6]([OH:18])[CH2:7][CH:8]([OH:17])[CH:9]=[CH:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH3:21]

Participants

4

Reactant 2

HCID 5003444Sodium cyanoborohydrideHCID 54551573N,N-diethyl-7-phenyl-5-hydroxy-3-oxo-6-heptenamide

Product 1

HCID 54030271N,N-diethyl-7-phenyl-3,5-dihydroxy-6-heptenamideYield 70%

Reagents, catalysts & solvents 1

HCID 3084342Chlorotitanium triisopropoxideCatalyst

Procedure

By carrying out the reaction as in Example 9 but starting from 530 mg of N,N-diethyl-7-phenyl-5-hydroxy-3-oxo-6-heptenamide (1.83 mmol), 0.51 cm3 of 95% titanium chloride triisopropoxide (2.2 mmol) and from 136.9 mg of 95% sodium cyanoborohydride (2.06 mmol), there is obtained, with a yield of 70%, 370 mg of N,N-diethyl-7-phenyl-3,5-dihydroxy-6-heptenamide for which the syn/anti ratio is equal to 70/30.

Workup

  1. customthe reaction as in Example 9

Sources & evidence

ORD record
ord-869744512130450cb39d4333c8a7033e
Source dataset
uspto-grants-1994_09
Patent number
US05347039

Reaction notes

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