Sodium cyanoborohydride → S-t-butyl 5-phenyl-3,5-dihydroxypentanethioate

HRID 2226279Notes

Reaction equation

HRID 2226279 reaction equation
[C:1]1([CH:7]([OH:19])[CH2:8][C:9](=[O:18])[CH2:10][C:11](=[O:17])[S:12][C:13]([CH3:16])([CH3:15])[CH3:14])[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]([OH:19])[CH2:8][CH:9]([OH:18])[CH2:10][C:11](=[O:17])[S:12][C:13]([CH3:16])([CH3:14])[CH3:15])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 5003444Sodium cyanoborohydrideHCID 19003813S-t-butyl 5-Phenyl-5-hydroxy-3-oxopentanethioate

Product 1

HCID 19003820S-t-butyl 5-phenyl-3,5-dihydroxypentanethioateYield 79.6%

Reagents, catalysts & solvents 1

HCID 3084342Chlorotitanium triisopropoxideCatalyst

Procedure

By carrying out the reaction as in Example 9 but starting from 500 mg of S-t-butyl 5-Phenyl-5-hydroxy-3-oxopentanethioate (1.78 mmol), 0.49 cm3 of titanium chloride triisopropoxide (1.96 mmol) and from 131.9 mg of sodium cyanoborohydride, there is obtained, after 3 hours 40 minutes, with a yield of 79.5%, 400 mg of S-t-butyl 5-phenyl-3,5-dihydroxypentanethioate for which the syn/anti ratio is equal to 90/10.

Workup

  1. customthe reaction as in Example 9

Sources & evidence

ORD record
ord-c843b45b1986430793db6bd5e8912e37
Source dataset
uspto-grants-1994_09
Patent number
US05347039

Reaction notes

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