2,2,2-Trichloroethyl chloroformate → (-)-3-Acetylmorphinan-17-carboxylic acid (trichloroethyl)ester
Reaction equation
[C:1]([C:4]1[CH:5]=[CH:6][C:7]2[CH2:8][C@H:9]3[N:20](C)[CH2:19][CH2:18][C@@:15]4([C:16]=2[CH:17]=1)[C@H:10]3[CH2:11][CH2:12][CH2:13][CH2:14]4)(=[O:3])[CH3:2].Cl[C:23]([O:25][CH2:26][C:27]([Cl:30])([Cl:29])[Cl:28])=[O:24]>C1C=CC=CC=1.CCOCC.C(=O)([O-])[O-].[K+].[K+]>[Cl:28][C:27]([Cl:30])([Cl:29])[CH2:26][O:25][C:23]([N:20]1[CH2:19][CH2:18][C@@:15]23[C:16]4[CH:17]=[C:4]([C:1](=[O:3])[CH3:2])[CH:5]=[CH:6][C:7]=4[CH2:8][C@@H:9]1[C@@H:10]2[CH2:11][CH2:12][CH2:13][CH2:14]3)=[O:24]Participants
6
Reactant 2
Product 1
Reagents, catalysts & solvents 3
Procedure
To a mixture of 2.7 g of (-)-3-acetyl-N-methylmorphinan, 50 ml of benzene and 20 mg of potassium carbonate, was added dropwise 2.11 g of 2,2,2-trichloroethyl chloroformate in 10 ml of benzene. The reaction mixture was stirred at reflux temperature for 48 hours and after cooling it was diluted with 100 ml ether. The ether solution was extracted with 1 N hydrochloric acid (2×30 ml) and dried over magnesium sulfate. Removal of the solvent gave 2.8 g (66%) of crude (-)-3-acetylmorphinan-17-carboxylic acid (trichloroethyl)ester. For analysis, a sample of this compound was distilled, bp 230°-240° (0.1 mm), [α]25D-127.21° (c 1.11, MeOH).
Workup
- temperatureat reflux temperature for 48 hours
- temperatureafter cooling it
- extractionThe ether solution was extracted with 1 N hydrochloric acid (2×30 ml)
- dry with materialdried over magnesium sulfate
- customRemoval of the solvent
Sources & evidence
- ORD record
- ord-0cee517ca2e54920b05cb77755efe80c
- Source dataset
- uspto-grants-1983_02
- Patent number
- US04374139
Reaction notes
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