2-Butene, 1-bromo-3-methyl- → (-)-1-[17-(3-Methyl-2-butenyl)morphinan-3-yl]ethanone

HRID 1758508ノート

反応式

HRID 1758508 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+].[CH3:26][C:27]([CH3:31])=[CH:28][CH2:29]Br>CN(C)C=O>[CH3:26][C:27]([CH3:31])=[CH:28][CH2:29][N:15]1[CH2:16][CH2:17][C@@:6]23[C:5]4[CH:4]=[C:3]([C:18](=[O:20])[CH3:19])[CH:2]=[CH:1][C:14]=4[CH2:13][C@@H:12]1[C@@H:11]2[CH2:10][CH2:9][CH2:8][CH2:7]3

参加物

5

反応物 3

HCID 700922-Butene, 1-bromo-3-methyl-HCID 516892Sodium BicarbonateHCID 13100586HCID 13100586、化合物

生成物 1

HCID 13100605(-)-1-[17-(3-Methyl-2-butenyl)morphinan-3-yl]ethanone収率 93.1%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a mixture of 1.8 g of (-)-1-(morphinan-3-yl)ethanone, 0.6 g of sodium bicarbonate and 25 ml of dimethylformamide, was added 1.0 g of dimethylallyl bromide. After the mixture had been heated at 50° for 16 hours, it was cooled to room temperature and filtered. The filtrate was concentrated under reduced pressure and the residue was partitioned between 50 ml of methylene chloride and 30 ml of water. The methylene chloride solution was washed with water and dried over magnesium sulfate. Removal of the solvent gave 2.1 g (93%) of crude (-)-1-[17-(3-methyl-2-butenyl)morphinan-3-yl]ethanone. For analysis, a sample of this compound was distilled, bp 185°-195° (0.05 mm), [α]25D-76.53° (c 0.98, MeOH).

後処理

  1. temperatureAfter the mixture had been heated at 50° for 16 hours
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customthe residue was partitioned between 50 ml of methylene chloride and 30 ml of water
  5. washThe methylene chloride solution was washed with water
  6. dry with materialdried over magnesium sulfate
  7. customRemoval of the solvent

出典と根拠

ORDレコード
ord-7dd742878f7a437b8fa4a841a19ef86a
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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