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

HRID 1168006노트

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HRID 1168006 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

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온도
0 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-86844d447f284faebbaee7e013ee3f64
출처 데이터셋
uspto-grants-2003_09
특허 번호
US06620964B2

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