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

HRID 1168006ノート

反応式

HRID 1168006 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
0 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-86844d447f284faebbaee7e013ee3f64
出典データセット
uspto-grants-2003_09
特許番号
US06620964B2

反応ノート

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