(Chloromethyl)cyclopropane → 3-Acetyl-N-(cyclpropylmethyl)morphinan

HRID 1758504노트

반응식

HRID 1758504 반응식
[CH:1]1[C:14]2[CH2:13][C@H:12]3[NH:15][CH2:16][CH2:17][C@:6]4([C@H:11]3[CH2:10][CH2:9][CH2:8][CH2:7]4)[C:5]=2[CH:4]=[C:3]([C:18](=[O:20])[CH3:19])[CH:2]=1.C(=O)(O)[O-].[Na+].[CH:26]1([CH2:29]Cl)[CH2:28][CH2:27]1>CN(C)C=O>[CH:26]1([CH2:29][N:15]2[CH2:16][CH2:17][C@@:6]34[C:5]5[CH:4]=[C:3]([C:18](=[O:20])[CH3:19])[CH:2]=[CH:1][C:14]=5[CH2:13][C@@H:12]2[C@@H:11]3[CH2:10][CH2:9][CH2:8][CH2:7]4)[CH2:28][CH2:27]1

참가 물질

5

반응물 3

HCID 80013(Chloromethyl)cyclopropaneHCID 516892Sodium BicarbonateHCID 13100586HCID 13100586, 화합물

생성물 1

HCID 54918993-Acetyl-N-(cyclpropylmethyl)morphinan수율 83.3%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a mixture of 0.8 g of (-)-1-(morphinan-3-yl)-ethanone, 0.6 g of sodium bicarbonate and 10 ml dimethylformamide, was added 0.3 g of cyclopropylmethyl chloride. After the mixture had been heated at reflux for 18 hours, it was cooled to room temperature and filtered. The filtrate was concentrated under reduced pressure and the residue was dissolved in 60 ml ether. The ether solution was washed with water, dried over magnesium sulfate and removal of the solvent gave 0.8 g (83%) of crude (-)-1-[N-(cyclopropylmethyl)morphinan-3-yl]ethanone. For analysis, a sample of this compound was distilled, bp 185°-195° (0.1 mm), [α]25D-83.21° (c 1.02, MeOH).

후처리

  1. temperatureAfter the mixture had been heated
  2. temperatureat reflux for 18 hours
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. dissolutionthe residue was dissolved in 60 ml ether
  6. washThe ether solution was washed with water
  7. dry with materialdried over magnesium sulfate and removal of the solvent

출처 및 근거

ORD 기록
ord-b0fc39813b9e4326a079a76273774dbd
출처 데이터셋
uspto-grants-1983_02
특허 번호
US04374139

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