Sodium cyanoborohydride → t-Butyl 5-phenyl-3,5-dihydroxypentanoate

HRID 2226277Notes

Reaction equation

HRID 2226277 reaction equation
[C:1]1([CH:7]([OH:19])[CH2:8][C:9](=[O:18])[CH2:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[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:13][C:14]([CH3:15])([CH3:17])[CH3:16])=[O:12])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 5003444Sodium cyanoborohydrideHCID 12202119t-Butyl 5-phenyl-5-hydroxy-3-oxopentanoate

Product 1

HCID 18967272t-Butyl 5-phenyl-3,5-dihydroxypentanoateYield 68%

Reagents, catalysts & solvents 1

HCID 3084342Chlorotitanium triisopropoxideCatalyst

Procedure

By carrying out the reaction as in Example 9 but starting from 1.06 g of t-butyl 5-phenyl-5-hydroxy-3-oxopentanoate and using 1.05 cm3 of titanium chloride triisopropoxide (4.17 mmol) and 281.4 mg of sodium cyanoborohydride (4.24 mmol), there is obtained, after reacting for 3 hours 30 minutes, with a yield of 68%, 720 mg of t-butyl 5-phenyl-3,5-dihydroxypentanoate for which the syn/anti ratio is equal to 95/5.

Workup

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

Sources & evidence

ORD record
ord-b97895097e194d0fbacb05a9affdefd7
Source dataset
uspto-grants-1994_09
Patent number
US05347039

Reaction notes

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