Potassium Iodide → 6-Ketonalbuphine

HRID 39326

반응식

HRID 39326 반응식
[CH3:1][N:2]1[C@@H:12]2[CH2:13][C:14]3[CH:19]=[CH:18][C:17]([OH:20])=[C:16]4[O:21][C@H:6]5[C:7]([CH:9]=[CH:10][C@:11]2([OH:22])[C@:5]5([C:15]=34)[CH2:4][CH2:3]1)=[O:8].C(=O)([O-])[O-].[K+].[K+].[I-].[K+].BrC[CH:33]1[CH2:36][CH2:35][CH2:34]1>CC(N(C)C)=O>[CH2:33]1[CH2:36][CH:35]([CH2:1][N:2]2[C@@H:12]3[CH2:13][C:14]4[CH:19]=[CH:18][C:17]([OH:20])=[C:16]5[O:21][C@H:6]6[C:7]([CH2:9][CH2:10][C@:11]3([OH:22])[C@:5]6([C:15]=45)[CH2:4][CH2:3]2)=[O:8])[CH2:34]1

참가 물질

6

반응물 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 2734658(Bromomethyl)cyclobutane2회HCID 1528625314-Hydroxymorphine-6-one2회

생성물 1

HCID 444650036-Ketonalbuphine수율 73.2%

시약·촉매·용매 1

HCID 31374Dimethylacetamide용매

실험 절차

Noroxymorphone (1.59 g, 5.5 mmol), potassium carbonate (0.61 g, 6.1 mmol), potassium iodide (0.46 g, 2.8 mmol), and dimethyl acetamide (10 mL) were added into a round bottom flask. Bromomethylcyclobutane (0.82 g, 5.5 mmol, 0.62 mL) was added. The reaction was stirred for 7 days at room temperature. At that time, bromomethylcyclobutane (0.82 g, 5.5 mmol, 0.62 mL) was added. The reaction was stirred for an additional 7 days. HPLC analysis indicated that the noroxymorphone was consumed. Distilled water (50 mL) was added and stirred at room temperature for 6 hours. An off-white precipitate formed, which was removed by filtration. The solid was washed with distilled water (25 mL), then slurried for 24 hours in acetonitrile (25 mL). Filtration, washing the solid with acetonitrile (10 mL), and drying at room temperature under vacuum for 24 hours yielded N-(cyclobutylmethyl)-noroxymorphone (1.43 g, 73% yield) as a tan solid.

후처리

  1. stirringThe reaction was stirred for an additional 7 days
  2. customwas consumed
  3. additionDistilled water (50 mL) was added
  4. stirringstirred at room temperature for 6 hours
  5. customAn off-white precipitate formed
  6. customwhich was removed by filtration
  7. washThe solid was washed with distilled water (25 mL)
  8. waitslurried for 24 hours in acetonitrile (25 mL)
  9. filtrationFiltration
  10. washwashing the solid with acetonitrile (10 mL)
  11. customdrying at room temperature under vacuum for 24 hours

출처 및 근거

ORD 기록
ord-51eb604ae3e04854819ac25796e786bd
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08524904B2

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