m-Chloroperbenzoic acid → racemic (1S,4R,7R)-4-methyl-8-oxa-3-aza-bicyclo[5.1.0]octane-3-carboxylic acid benzyl ester

HRID 229794

반응식

HRID 229794 반응식
ClC1C=CC=C(C(OO)=[O:9])C=1.[CH2:12]([O:19][C:20]([N:22]1[CH2:28][CH:27]=[CH:26][CH2:25][CH2:24][CH:23]1[CH3:29])=[O:21])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C(Cl)Cl>[CH2:12]([O:19][C:20]([N:22]1[CH:23]([CH3:29])[CH2:24][CH2:25][CH:26]2[CH:27]([O:9]2)[CH2:28]1)=[O:21])[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

참가 물질

4

반응물 2

HCID 70297m-Chloroperbenzoic acid2회HCID 11586812Benzyl 2-methyl-2,3,4,7-tetrahydro-1H-azepine-1-carboxylate

생성물 1

HCID 21036429racemic (1S,4R,7R)-4-methyl-8-oxa-3-aza-bicyclo[5.1.0]octane-3-carboxylic acid benzyl ester수율 50.4%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

m-Chloro-perbenzoic acid (1.05 g, 57-86% pure) was added to a solution of 2-methyl-2,3,4,7-tetrahydro-azepine-1-carboxylic acid benzyl ester (0.83 g, 3.34 mmol) in CH2Cl2 at 0 degrees C. The reaction mixture was stirred for half an hour, then was warmed to RT. Additional m-chloro-perbenzoic acid (0.3 g, 57-86% pure) was added and the reaction was stirred 2 h. The reaction mixture was concentrated in vacuo by rotary evaporation, then 80 ml of 9:1 hexanes/EtOAc was added and the reaction mixture was filtered. The filtrate was concentrated in vacuo by rotary evaporation, then was chromatographed (silica gel, 20% EtOAc:hexanes) to give racemic (1S,4R,7S)-4-methyl-8-oxa-3-aza-bicyclo[5.1.0]octane-3-carboxylic acid benzyl ester (0.44 g, 50%) and the title compound as a racemic mixture of the title compound (0.15 g, 17% yield): 1H NMR: 7.42-7.22 (m, 5H), 5.13 (2H, s), 4.50-4.15 (m, 2H), 3.27 (1H, d), 3.12-2.95 (1H, m), 2.15-1.70 (m, 2H), 1.47 (m, 2H), 1.12 (3H, d); Liquid Chromatgraphy/Electrospray mass spec: M+H+=262.0.

후처리

  1. stirringthe reaction was stirred 2 h
  2. concentrationThe reaction mixture was concentrated in vacuo by rotary evaporation
  3. addition80 ml of 9:1 hexanes/EtOAc was added
  4. filtrationthe reaction mixture was filtered
  5. concentrationThe filtrate was concentrated in vacuo by rotary evaporation
  6. customwas chromatographed (silica gel, 20% EtOAc:hexanes)

출처 및 근거

ORD 기록
ord-c798ac486c874d588007831647fcb45f
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07563784B2

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