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

HRID 1758504ノート

反応式

HRID 1758504 の反応式
[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

参加物

5

反応物 3

HCID 80013(Chloromethyl)cyclopropaneHCID 516892Sodium BicarbonateHCID 13100586HCID 13100586、化合物

生成物 1

HCID 54918993-Acetyl-N-(cyclpropylmethyl)morphinan収率 83.3%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-b0fc39813b9e4326a079a76273774dbd
出典データセット
uspto-grants-1983_02
特許番号
US04374139

反応ノート

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