(-)-3-Acetylmorphinan-17-carboxylic acid (trichloroethyl)ester → HCID 13100586, compound
Reaction equation
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]=1Participants
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
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).
Workup
- filtrationfiltered
- concentrationThe filtrate was concentrated in vacuo
- customthe residue was partitioned between 40 ml ether and dilute ammonium hydroxide
- extractionThe ether solution was extracted with 60 ml of 4 N hydrochloric acid
- extractionextracted with ether (2×30 ml)
- dry with materialThe ether solution was dried over magnesium sulfate and removal of the solvent
Sources & evidence
- ORD record
- ord-5a760000605a48baab7f1b08cf0696aa
- Source dataset
- uspto-grants-1983_02
- Patent number
- US04374139
Reaction notes
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