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

HRID 30516

反応式

HRID 30516 の反応式
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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-a915ccb62cee4ba8b6552be00937a3f4
出典データセット
uspto-grants-2008_09
特許番号
US07423169B2

関連ノート

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