(S)-alpha-[(t-butylsulphonyl)methyl]hydrocinnamic acid → (S)-alpha-[(tert-butylsulphonyl)methyl]cyclohexanepropionic acid

HRID 2294687노트

반응식

HRID 2294687 반응식
[C:1]([S:5]([CH2:8][C@@H:9]([CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:10]([OH:12])=[O:11])(=[O:7])=[O:6])([CH3:4])([CH3:3])[CH3:2]>[Rh].[O-2].[Al+3].[O-2].[O-2].[Al+3].C(O)C>[C:1]([S:5]([CH2:8][C@@H:9]([CH2:13][CH:14]1[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]1)[C:10]([OH:12])=[O:11])(=[O:6])=[O:7])([CH3:4])([CH3:2])[CH3:3]

참가 물질

4

반응물 1

HCID 9860623(S)-alpha-[(t-butylsulphonyl)methyl]hydrocinnamic acid

생성물 1

HCID 22879414(S)-alpha-[(tert-butylsulphonyl)methyl]cyclohexanepropionic acid수율 78.7%

시약·촉매·용매 2

HCID 131712135Rhodium aluminium oxide촉매HCID 702Ethanol용매

실험 절차

A mixture of 2 g (7 mmol) of (S)-α-[(tert-butylsulphonyl)methyl]hydrocinnamic acid (EPA 0236734) and 2 g of rhodium/aluminium oxide catalyst (5%) in 100 ml of ethanol is hydrogenated for 10 hours at 50° and 10 bar. After filtering off the catalyst the reaction solution is evaporated under reduced pressure and the residue is recrystallized from a 9:1 mixture of hexane and ethyl acetate. There are obtained 1.6 g of (S)-α-[(tert-butylsulphonyl)methyl]cyclohexanepropionic acid as colourless needles; MS: 308 (M+NH4)+.

후처리

  1. filtrationAfter filtering off the catalyst the reaction solution
  2. customis evaporated under reduced pressure
  3. customthe residue is recrystallized from a 9:1 mixture of hexane and ethyl acetate

출처 및 근거

ORD 기록
ord-0cc4981f753440e78dbafa52965568cd
출처 데이터셋
uspto-grants-1997_11
특허 번호
US05688946

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