4-Methylmorpholine → Allyl 1-{[(alpha-Chloroethoxy)carbonyl]aminomethyl}-1-Cyclohexane Acetate

HRID 30516

반응식

HRID 30516 반응식
Cl.[NH2:2][CH2:3][C:4]1([CH2:10][C:11]([O:13][CH2:14][CH:15]=[CH2:16])=[O:12])[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]1.Cl[C:18]([O:20][CH:21]([Cl:23])[CH3:22])=[O:19].CN1CCOCC1>ClCCl.C(OCC)C>[Cl:23][CH:21]([O:20][C:18]([NH:2][CH2:3][C:4]1([CH2:10][C:11]([O:13][CH2:14][CH:15]=[CH2:16])=[O:12])[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]1)=[O:19])[CH3:22]

참가 물질

6

반응물 3

HCID 79724-MethylmorpholineHCID 5213051-Chloroethyl chloroformateHCID 66743418Prop-2-enyl 2-[1-(aminomethyl)cyclohexyl]acetate;hydrochloride

생성물 1

HCID 9995975Allyl 1-{[(alpha-Chloroethoxy)carbonyl]aminomethyl}-1-Cyclohexane Acetate수율 100.5%

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 6344Dichloromethane용매

반응 조건

온도
0 °C

실험 절차

To a solution of compound (13) (30 g, 0.121 mol) in dichloromethane (100 mL) was slowly added 1-chloroethyl chloroformate (13 mL, 16.9 g, 0.119 mol). The reaction mixture was cooled to 0° C. and N-methylmorpholine (26.39 mL, 24.28 g, 0.24 mol) was slowly added over a period of 1 h while maintaining a temperature of less than 10° C. The resulting turbid solution was stirred for 30 min, and the reaction mixture was then diluted with diethyl ether (250 mL), washed with water (100 mL) and brine (100 mL). The organic phase was dried over anhydrous sodium sulfate and concentrated to give the desired product (14) as light yellow viscous liquid (38 g, 99% yield). 1H NMR (CDCl3, 400 MHz): δ 1.35-1.58 (m, 10H), 1.78 (d, 3H), 2.32 (s, 2H), 3.22 (d, 2H), 4.57 (d, 2H), 5.25 (dd, 1H), 5.32 (dd, 1H), 5.52 (br. s, 1H), 5.90-5.94 (m, 1H), 6.54 (q, 1H).

후처리

  1. temperaturewhile maintaining a temperature of less than 10° C
  2. washwashed with water (100 mL) and brine (100 mL)
  3. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  4. concentrationconcentrated

출처 및 근거

ORD 기록
ord-a915ccb62cee4ba8b6552be00937a3f4
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07423169B2

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