Sodium borohydride → Methyl (6S)-6,8-dihydroxyoctanoate

HRID 1168006Notes

Reaction equation

HRID 1168006 reaction equation
[OH:1][C@@H:2]([CH2:8][CH2:9][CH2:10][CH2:11][C:12]([O:14][CH3:15])=[O:13])[CH2:3][C:4](OC)=[O:5].[BH4-].[Na+].B([O-])([O-])OC>CO>[OH:1][C@H:2]([CH2:3][CH2:4][OH:5])[CH2:8][CH2:9][CH2:10][CH2:11][C:12]([O:14][CH3:15])=[O:13]

Participants

5

Reactant 3

HCID 4311764Sodium borohydrideHCID 9859249dimethyl (3S)-3-hydroxyoctanedioateHCID 71359510Methylborate

Product 1

HCID 10899438Methyl (6S)-6,8-dihydroxyoctanoateYield 90%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

45.3 g (0.2 mol) of enantiomerically pure dimethyl (3S)-3-hydroxyoctanedioate were mixed in a Haake kneader at from 30 to 40° C. with 5.2 g of sodium borohydride (0.14 mol, 0.7 equivalents). The reaction mixture was kneaded until the reaction was complete (TLC monitoring, 40 min). The intermediate methyl borate was then taken up in methanol and hydrolyzed under acidic conditions. The desired methyl (6S)-6,8-dihydroxyoctanoate was extracted with ethyl acetate. After drying the organic phase, this was cooled to 0° C., and the product which crystallized out was filtered off. 34.5 g of methyl (6S)-6,8-dihydroxyoctanoate in the form of white crystals were obtained (90% yield).

Workup

  1. custom(TLC monitoring, 40 min)
  2. extractionThe desired methyl (6S)-6,8-dihydroxyoctanoate was extracted with ethyl acetate
  3. customAfter drying the organic phase
  4. customthe product which crystallized out
  5. filtrationwas filtered off

Sources & evidence

ORD record
ord-86844d447f284faebbaee7e013ee3f64
Source dataset
uspto-grants-2003_09
Patent number
US06620964B2

Reaction notes

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