Hydrochloric Acid → 17-cyclobutylmethyl-3-methoxy-8beta-methyl-6-methylene-morphinane Hydrochloride

HRID 128212

반응식

HRID 128212 반응식
[CH2:1]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[CH:21]1([CH2:25][N:26]2[CH2:44][CH2:43][C@@:33]34[C:34]5[CH:35]=[C:36]([O:41][CH3:42])[CH:37]=[CH:38][C:39]=5[CH2:40][C@@H:27]2[C@@H:28]3[C@@H:29]([CH3:46])[CH2:30][C:31](=O)[CH2:32]4)[CH2:24][CH2:23][CH2:22]1.[ClH:47]>CS(C)=O>[ClH:47].[CH:21]1([CH2:25][N:26]2[CH2:44][CH2:43][C@@:33]34[C:34]5[CH:35]=[C:36]([O:41][CH3:42])[CH:37]=[CH:38][C:39]=5[CH2:40][C@@H:27]2[C@@H:28]3[C@@H:29]([CH3:46])[CH2:30][C:31](=[CH2:1])[CH2:32]4)[CH2:22][CH2:23][CH2:24]1

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 137960MethylenetriphenylphosphoraneHCID 5661625317-Cyclobutylmethyl-3-methoxy-8beta-methyl-morphinan-6-one

생성물 1

HCID 7052792317-cyclobutylmethyl-3-methoxy-8beta-methyl-6-methylene-morphinane Hydrochloride수율 37%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

실험 절차

To a solution of methylenetriphenylphosphorane (14.4 mmole) in dimethyl sulfoxide (30 ml) prepared in the usual fashion was added a solution of 17-cyclobutylmethyl-3-methoxy-8β-methyl-morphinan-6-one. The reaction was heated at 75° for 2 hours under an atmosphere of nitrogen. Workup followed by chromatography gave the free base of TR-5377 as a foam. This was converted to the HCl salt which was crystallized from toluene to give 860 mg (37%) of TR-5377, mp. 221°-224°.

후처리

  1. temperatureThe reaction was heated at 75° for 2 hours under an atmosphere of nitrogen
  2. customgave the free base of TR-5377 as a foam
  3. customwas crystallized from toluene

출처 및 근거

ORD 기록
ord-053c919ec2d24faf9efa89f8a53d82a8
출처 데이터셋
uspto-grants-1981_03
특허 번호
US04259329

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