Potassium Carbonate → (-)-3-acetyl-N-cyclobutylmethylmorphinan

HRID 1758505ノート

反応式

HRID 1758505 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-].[K+].[K+].[CH:27]1([CH2:31]Cl)[CH2:30][CH2:29][CH2:28]1>CN(C)C=O>[C:18]([C:3]1[CH:2]=[CH:1][C:14]2[CH2:13][C@H:12]3[N:15]([CH2:31][CH:27]4[CH2:30][CH2:29][CH2:28]4)[CH2:16][CH2:17][C@@:6]4([C:5]=2[CH:4]=1)[C@H:11]3[CH2:10][CH2:9][CH2:8][CH2:7]4)(=[O:20])[CH3:19]

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 13100586HCID 13100586、化合物HCID 23446147(Chloromethyl)cyclobutane

生成物 1

HCID 13100589(-)-3-acetyl-N-cyclobutylmethylmorphinan収率 76%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a mixture of 1.7 g, (-)-1-(morphinan-3-yl)ethanone, 1.5 g of potassium carbonate and 40 ml dimethylformamide, was added 1.2 g of cyclobutylmethyl chloride. After the mixture had been heated at 100°-110° for 16 hours it was cooled to room temperature and filtered. The filtrate was concentrated under reduced pressure and the residue was dissolved in 120 ml of ether. The ether solution was washed with water (2×20 ml), dried over magnesium sulfate and removal of the solvent gave 1.6 g (76%) of crude (-)-3-acetyl-N-cyclobutylmethylmorphinan. For analysis, a sample of this compound was distilled, bp 200°-210° (0.05 mm), [α]25D-80.64° (c 1.03, MeOH).

後処理

  1. temperatureAfter the mixture had been heated at 100°-110° for 16 hours it
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. dissolutionthe residue was dissolved in 120 ml of ether
  5. washThe ether solution was washed with water (2×20 ml)
  6. dry with materialdried over magnesium sulfate and removal of the solvent

出典と根拠

ORDレコード
ord-fd72a3eb433e4cdca7b00a1df87b90f1
出典データセット
uspto-grants-1983_02
特許番号
US04374139

反応ノート

読み込み中…