Divinyl sulfone → 3-(1,1-Dioxo-1-thiomorpholine-4-YL)azetidine-1-carboxylic acid tert-butyl ester

HRID 1922651노트

반응식

HRID 1922651 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:11][CH:10]([NH2:12])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH:13]([S:15]([CH:18]=[CH2:19])(=[O:17])=[O:16])=[CH2:14]>CCO>[C:1]([O:5][C:6]([N:8]1[CH2:11][CH:10]([N:12]2[CH2:19][CH2:18][S:15](=[O:17])(=[O:16])[CH2:13][CH2:14]2)[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

참가 물질

4

반응물 2

HCID 6496Divinyl sulfoneHCID 1516507Tert-butyl 3-aminoazetidine-1-carboxylate

생성물 1

HCID 596054113-(1,1-Dioxo-1-thiomorpholine-4-YL)azetidine-1-carboxylic acid tert-butyl ester수율 64%

시약·촉매·용매 1

HCID 702Ethanol용매2회

실험 절차

To a refluxing solution of 3-aminoazetidine-1-carboxylic acid tert-butyl ester (10.0 g, 58.1 mmol) in EtOH (50 mL) was added drop wise a solution of divinyl sulfone (5.9 mL, 6.86 g, 58.1 mmol) in EtOH (50 mL) The resulting mixture was stirred at reflux for 15.5 h, cooled to room temperature and concentrated in vacuo. The resulting beige solid was triturated with Et2O, affording the title compound as a white solid (10.8 g, 64%). 1H NMR (CDCl3, 300 MHz): δ 3.97 (dd, J=8.8, 7.1 Hz, 2H); 3.76 (dd, J=8.8, 7.1 Hz, 2H); 3.36-3.26 (m, 1H); 3.13-3.05 (m, 4H); 2.90-2.83 (m, 4H); 1.44 (s, 9H).

후처리

  1. temperatureat reflux for 15.5 h
  2. concentrationconcentrated in vacuo
  3. customThe resulting beige solid was triturated with Et2O

출처 및 근거

ORD 기록
ord-77d7bf5b085f475ca271f2d04f688fa2
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08173650B2

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