(-)-3-Acetylmorphinan-17-carboxylic acid (trichloroethyl)ester → HCID 13100586, 화합물

HRID 1758503노트

반응식

HRID 1758503 반응식
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

참가 물질

4

반응물 1

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

생성물 1

HCID 13100586HCID 13100586, 화합물수율 71%

시약·촉매·용매 2

HCID 23994Zinc촉매HCID 176Acetic Acid용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-5a760000605a48baab7f1b08cf0696aa
출처 데이터셋
uspto-grants-1983_02
특허 번호
US04374139

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