Methyl 3-oxovalerate → Methyl (S)-3-hydroxypentanoate

HRID 857537노트

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HRID 857537 반응식
[O:1]=[C:2]([CH2:8][CH3:9])[CH2:3][C:4]([O:6][CH3:7])=[O:5]>CO>[OH:1][C@@H:2]([CH2:8][CH3:9])[CH2:3][C:4]([O:6][CH3:7])=[O:5]

참가 물질

3

반응물 1

HCID 121699Methyl 3-oxovalerate

생성물 1

HCID 10290819Methyl (S)-3-hydroxypentanoate수율 90%

시약·촉매·용매 1

HCID 887Methanol용매

반응 조건

온도
80 °C

실험 절차

To a solution of 6.22 mg (48 mmol) of methyl 3-ketovalerate in 48 ml methanol, 36 mg (0.004 mmol) RuCl2(S)-binap was added and stirred in an autoclave under a hydrogen pressure of 30 atm at 80° C. for 66 hours. After concentration and distillation, 5.71 g (43.2 mmol, 97% ee) of methyl (S)-3-hydroxyvalerate was obtained. The condition of chiral HPLC is the following. Column, CHIRALPAK OD manufactured by Daicel Chemical Industries, Ltd.; Eluate, Hexane:2-propanol=95:5; flow rate, 1.0 mL/min; Wavelength of detection, 210 nm; Temperature, 25° C.; Retention time, 15 min (R) and 27 min (S).

후처리

  1. concentrationAfter concentration and distillation

출처 및 근거

ORD 기록
ord-fd977c8e2a464afc8b7fac7f44d2c62c
출처 데이터셋
uspto-grants-2006_12
특허 번호
US07145030B2

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