Reaction equation
[CH3:1][N:2]1[CH2:21][CH2:20][C@:9]23[C:10]4[C:11]5[O:19][C@H:8]2[C:7](=[O:22])[CH2:6][CH2:5][C@H:4]3[C@H:3]1[CH2:16][C:15]=4[CH:14]=[CH:13][C:12]=5[O:17][CH3:18].[OH-].[Na+].C(S(O)=O)(N)=N.N#N>C(O)C.CO>[CH3:1][N:2]1[C@@H:3]2[CH2:16][C:15]3[CH:14]=[CH:13][C:12]([O:17][CH3:18])=[C:11]4[O:19][C@H:8]5[C@H:7]([OH:22])[CH2:6][CH2:5][C@@H:4]2[C@:9]5([C:10]=34)[CH2:20][CH2:21]1Participants
Procedure
75 mg. (0.25 mmol.) of 17-methyl-4,5α-epoxy-3-methoxymorphinan-6-one is dissolved in 20 ml. of methanol. The resulting solution is treated with 10 ml. of aqueous sodium hydroxide (150 mg.) containing 95 mg. (0.88 mmol.) formamidinesulfinic acid. The resulting mixture is magnetically stirred for one hour at 80° C. under a current of N2. The reaction mixture is thereafter stripped of ethanol and extracted with chloroform. Upon evaporation of chloroform, a residue of dihydroisocodeine is obtained. The NMR spectrum (CDCl3) of the dihydroisocodeine product is identical with that of the published reference spectrum (see S. Okuda et al., Chem. Pharm. Bull., 12, 104 (1964). The dihydroisocodeine free base is converted to its hydrochloride which has no melting point below 300° C.
Workup
- additionThe resulting solution is treated with 10 ml
- extractionextracted with chloroform
- customUpon evaporation of chloroform
Sources & evidence
- ORD record
- ord-f8ee8f43aef24b3bbfeb5ca0c5e8530d
- Source dataset
- uspto-grants-1978_05
- Patent number
- US04089855
Linked notes
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