(-)-3-Acetylmorphinan-17-carboxylic acid (trichloroethyl)ester → HCID 13100586、化合物

HRID 1758503ノート

反応式

HRID 1758503 の反応式
ClC(Cl)(Cl)COC([N:7]1[CH2:26][CH2:25][C@@:14]23[C:15]4[CH:16]=[C:17]([C:22](=[O:24])[CH3:23])[CH:18]=[CH:19][C:20]=4[CH2:21][C@@H:8]1[C@@H:9]2[CH2:10][CH2:11][CH2:12][CH2:13]3)=O>C(O)(=O)C.[Zn]>[CH:19]1[C:20]2[CH2:21][C@H:8]3[NH:7][CH2:26][CH2:25][C@:14]4([C@H:9]3[CH2:10][CH2:11][CH2:12][CH2:13]4)[C:15]=2[CH:16]=[C:17]([C:22](=[O:24])[CH3:23])[CH:18]=1

参加物

4

反応物 1

HCID 13100607(-)-3-Acetylmorphinan-17-carboxylic acid (trichloroethyl)ester

生成物 1

HCID 13100586HCID 13100586、化合物収率 71%

試薬・触媒・溶媒 2

HCID 23994Zinc触媒HCID 176Acetic Acid溶媒

実験手順

To a solution of 2.4 g of (-)-3-acetylmorphinan-17-carboxylic acid (trichloroethyl)ester in 40 ml of 90% acetic acid was added portionwise, 2.5 g of zinc-dust. The mixture was stirred at room temperature for 16 hours and filtered. The filtrate was concentrated in vacuo and the residue was partitioned between 40 ml ether and dilute ammonium hydroxide. The ether solution was extracted with 60 ml of 4 N hydrochloric acid. The acidic solution was basified with concentrated ammonium hydroxide and extracted with ether (2×30 ml). The ether solution was dried over magnesium sulfate and removal of the solvent gave 1.0 g (71%) of crude (-)-1-(morphinan-3-yl)ethanone. For analysis, a sample of this compound was distilled, bp 165°-175° (0.1 mm), [α]25D-24.77° (c 1.06, MeOH).

後処理

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated in vacuo
  3. customthe residue was partitioned between 40 ml ether and dilute ammonium hydroxide
  4. extractionThe ether solution was extracted with 60 ml of 4 N hydrochloric acid
  5. extractionextracted with ether (2×30 ml)
  6. dry with materialThe ether solution was dried over magnesium sulfate and removal of the solvent

出典と根拠

ORDレコード
ord-5a760000605a48baab7f1b08cf0696aa
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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