(S)-4-[(E)-2-(6-chloro-pyridin-3-yl)-vinyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester → (S)-4-[2-(6-chloro-pyridin-3-yl)-ethyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

HRID 1187778

반응식

HRID 1187778 반응식
[C:1]([O:5][C:6]([N:8]1[C@@H:12](/[CH:13]=[CH:14]/[C:15]2[CH:16]=[N:17][C:18]([Cl:21])=[CH:19][CH:20]=2)[CH2:11][O:10][C:9]1([CH3:23])[CH3:22])=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[Pt]>[C:1]([O:5][C:6]([N:8]1[C@@H:12]([CH2:13][CH2:14][C:15]2[CH:16]=[N:17][C:18]([Cl:21])=[CH:19][CH:20]=2)[CH2:11][O:10][C:9]1([CH3:23])[CH3:22])=[O:7])([CH3:4])([CH3:2])[CH3:3]

참가 물질

4

반응물 1

HCID 86664598(S)-4-[(E)-2-(6-chloro-pyridin-3-yl)-vinyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

생성물 1

HCID 86664597(S)-4-[2-(6-chloro-pyridin-3-yl)-ethyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester수율 94.3%

시약·촉매·용매 2

HCID 23939Platinum촉매HCID 887Methanol용매

실험 절차

To a stirred suspension of (S)-4-[(E)-2-(6-chloro-pyridin-3-yl)-vinyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (1.0 g) in methanol (70 ml) was added platinum on charcoal (0.58 g, 10 wt %) and the mixture was stirred under an atmosphere of hydrogen at room temperature for 15 min. The mixture was then filtered through celite and the filtrate was concentrated in vacuo to give (S)-4-[2-(6-chloro-pyridin-3-yl)-ethyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (949 mg, 94%) as a colourless oil. MS (ISP): 343.2 ([{37Cl}M+H]+), 341.1 ([{35Cl}M+H]+), 287.0 ([{37Cl}M+H—C4H8]+), 285.1 ([{35Cl}M+H—C4H8]+).

후처리

  1. filtrationThe mixture was then filtered through celite
  2. concentrationthe filtrate was concentrated in vacuo

출처 및 근거

ORD 기록
ord-e2dec380e5c843d6bdc4cc29bb60b0d4
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08673950B2

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