Pyridine → (RS)-1-acetyl-4-[4-(5-methoxymethyl-2-oxo-oxazolidin-3-yl)-phenyl]-piperidine

HRID 1900065노트

반응식

HRID 1900065 반응식
[CH3:1][O:2][CH2:3][CH:4]1[O:8][C:7](=[O:9])[N:6]([C:10]2[CH:15]=[CH:14][C:13]([CH:16]3[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]3)=[CH:12][CH:11]=2)[CH2:5]1.[C:22](OC(=O)C)(=[O:24])[CH3:23].N1C=CC=CC=1>C(Cl)Cl>[C:22]([N:19]1[CH2:20][CH2:21][CH:16]([C:13]2[CH:12]=[CH:11][C:10]([N:6]3[CH2:5][CH:4]([CH2:3][O:2][CH3:1])[O:8][C:7]3=[O:9])=[CH:15][CH:14]=2)[CH2:17][CH2:18]1)(=[O:24])[CH3:23]

참가 물질

5

반응물 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 23371817(RS)-4-[4-(5-methoxymethyl-2-oxo-oxazolidin-3-yl)-phenyl]-piperidine

생성물 1

HCID 23371884(RS)-1-acetyl-4-[4-(5-methoxymethyl-2-oxo-oxazolidin-3-yl)-phenyl]-piperidine수율 97.3%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

177.1 mg (0.61 mmol) of (RS)-4-[4-(5-methoxymethyl-2-oxo-oxazolidin-3-yl)-phenyl]-piperidine were dissolved in 20 ml of methylene chloride and treated with 68.5 mg (0.67 mmol) of acetic anhydride in the presence of 53.1 mg (0.67 mmol) of pyridine. After stirring at room temperature for 18 hours the mixture was washed with water and the organic phase was dried over sodium sulfate. After filtration and evaporation of the filtrate the product was dried in a high vacuum. 197.3 mg of (RS)-1-acetyl-4-[4-(5-methoxymethyl-2-oxo-oxazolidin-3-yl)-phenyl]-piperidine were obtained as a yellowish oil. 1H-NMR (CDCl3) ppm: 7.49 (d,2H), 7.20 (d,2H), 4.80 (m,2H), 4.05 (t, 1H), 3.92 (m,2H), 3.64 (d,2H), 3.43 (s,3H), 3.21 (m,1H), 2.68 (m,2H), 2.14 (s,3H), 1.85 (m,2H), 1.60 (m,2H).

후처리

  1. washwas washed with water
  2. dry with materialthe organic phase was dried over sodium sulfate
  3. filtrationAfter filtration and evaporation of the filtrate the product
  4. customwas dried in a high vacuum

출처 및 근거

ORD 기록
ord-3cfdfae420114e2e82e978e247292b6a
출처 데이터셋
uspto-grants-1996_11
특허 번호
US05574055

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