Sodium cyanoborohydride → t-Butyl 7-phenyl-3,5-dihydroxy-6-heptenoate

HRID 2226278Notes

Reaction equation

HRID 2226278 reaction equation
[C:1]1([CH:7]=[CH:8][CH:9]([OH:21])[CH2:10][C:11](=[O:20])[CH2:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([BH3-])#N.[Na+]>CC(C)[O-].CC(C)[O-].CC(C)[O-].[Cl-].[Ti+4]>[C:1]1([CH:7]=[CH:8][CH:9]([OH:21])[CH2:10][CH:11]([OH:20])[CH2:12][C:13]([O:15][C:16]([CH3:17])([CH3:18])[CH3:19])=[O:14])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 5003444Sodium cyanoborohydrideHCID 53985335t-Butyl 7-phenyl-5-hydroxy-3-oxo-6-heptenoate

Product 1

HCID 53722944t-Butyl 7-phenyl-3,5-dihydroxy-6-heptenoateYield 55%

Reagents, catalysts & solvents 1

HCID 3084342Chlorotitanium triisopropoxideCatalyst

Procedure

By carrying out the reaction as in Example 9 but starting from 1.0 g of t-butyl 7-phenyl-5-hydroxy-3-oxo-6-heptenoate (3.42 mmol) and using 0.95 cm3 of titanium chloride triisopropoxide (3.77 mmol) and 261.8 mg of sodium cyanoborohydride (3.95 mmol), there is obtained, after reacting for 3 hours 10 minutes, with a yield of 55%, 550 mg of t-butyl 7-phenyl-3,5-dihydroxy-6-heptenoate for which the syn/anti ratio is equal to 90/10.

Workup

  1. customthe reaction as in Example 9
  2. customthere is obtained

Sources & evidence

ORD record
ord-6c3857cf6e2f495d9d57da5b36dda2b2
Source dataset
uspto-grants-1994_09
Patent number
US05347039

Reaction notes

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