Potassium Carbonate → (-)-3-acetyl-N-cyclobutylmethylmorphinan

HRID 1758505노트

반응식

HRID 1758505 반응식
[CH:1]1[C:14]2[CH2:13][C@H:12]3[NH:15][CH2:16][CH2:17][C@:6]4([C@H:11]3[CH2:10][CH2:9][CH2:8][CH2:7]4)[C:5]=2[CH:4]=[C:3]([C:18](=[O:20])[CH3:19])[CH:2]=1.C(=O)([O-])[O-].[K+].[K+].[CH:27]1([CH2:31]Cl)[CH2:30][CH2:29][CH2:28]1>CN(C)C=O>[C:18]([C:3]1[CH:2]=[CH:1][C:14]2[CH2:13][C@H:12]3[N:15]([CH2:31][CH:27]4[CH2:30][CH2:29][CH2:28]4)[CH2:16][CH2:17][C@@:6]4([C:5]=2[CH:4]=1)[C@H:11]3[CH2:10][CH2:9][CH2:8][CH2:7]4)(=[O:20])[CH3:19]

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 13100586HCID 13100586, 화합물HCID 23446147(Chloromethyl)cyclobutane

생성물 1

HCID 13100589(-)-3-acetyl-N-cyclobutylmethylmorphinan수율 76%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a mixture of 1.7 g, (-)-1-(morphinan-3-yl)ethanone, 1.5 g of potassium carbonate and 40 ml dimethylformamide, was added 1.2 g of cyclobutylmethyl chloride. After the mixture had been heated at 100°-110° for 16 hours it was cooled to room temperature and filtered. The filtrate was concentrated under reduced pressure and the residue was dissolved in 120 ml of ether. The ether solution was washed with water (2×20 ml), dried over magnesium sulfate and removal of the solvent gave 1.6 g (76%) of crude (-)-3-acetyl-N-cyclobutylmethylmorphinan. For analysis, a sample of this compound was distilled, bp 200°-210° (0.05 mm), [α]25D-80.64° (c 1.03, MeOH).

후처리

  1. temperatureAfter the mixture had been heated at 100°-110° for 16 hours it
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. dissolutionthe residue was dissolved in 120 ml of ether
  5. washThe ether solution was washed with water (2×20 ml)
  6. dry with materialdried over magnesium sulfate and removal of the solvent

출처 및 근거

ORD 기록
ord-fd72a3eb433e4cdca7b00a1df87b90f1
출처 데이터셋
uspto-grants-1983_02
특허 번호
US04374139

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