Diethyl Ether → 1-[(4R,4aR,7S,7aR,12bS)-7,9-dihydroxy-3-methyl-1,2,4,4a,7,7a,10,13-octahydro-4,12-methanobenzofuro[3,2-e]isoquinolin-9-yl]ethanone

HRID 53867

반응식

HRID 53867 반응식
[CH:1]1[C:17]2[CH2:16][C@H:15]3[N:18]([CH2:20][CH2:21][C@@:7]45[C@H:14]3[CH:13]=[CH:12][C@H:10]([OH:11])[C@@H:8]4[O:9][C:5]([C:6]=25)=[C:3]([OH:4])[CH:2]=1)[CH3:19].[C:22](OC(=O)C)(=[O:24])[CH3:23].CCOCC>C(=O)(O)[O-].[Na+]>[C:22]([C:3]1([OH:4])[C:5]2[O:9][C@@H:8]3[C@@:7]45[CH2:21][CH2:20][N:18]([CH3:19])[C@@H:15]([C@@H:14]4[CH:13]=[CH:12][C@@H:10]3[OH:11])[CH2:16][C:17]([C:6]5=2)=[CH:1][CH2:2]1)(=[O:24])[CH3:23]

참가 물질

5

반응물 3

HCID 3283Diethyl EtherHCID 7918Acetic AnhydrideHCID 5288826Morphine

생성물 1

HCID 222119501-[(4R,4aR,7S,7aR,12bS)-7,9-dihydroxy-3-methyl-1,2,4,4a,7,7a,10,13-octahydro-4,12-methanobenzofuro[3,2-e]isoquinolin-9-yl]ethanone수율 80%

시약·촉매·용매 1

HCID 516892Sodium Bicarbonate용매

실험 절차

To a stirred suspension of morphine (4 g, 14 mmol) in 10% aqueous sodium bicarbonate (377 ml) was added acetic anhydride (19 ml) over 8.5 minutes. 15 minutes after the addition, ice cold water (300 ml) was added and the solution was extracted with dichloromethane (200 ml). The organic extract was washed with brine, dried over Na2SO4, and the solvent removed in vacuo to leave a sticky white residue. Trituration with ether gave 3-acetylmorphine (3.68 g, 80%). The corresponding 3-pivalyl, 3-isobutyryl, 3-propionyl and other 3-acyl derivatives of morphine were also prepared.

후처리

  1. additionwas added
  2. extractionthe solution was extracted with dichloromethane (200 ml)
  3. extractionThe organic extract
  4. washwas washed with brine
  5. dry with materialdried over Na2SO4
  6. customthe solvent removed in vacuo
  7. customto leave a sticky white residue

출처 및 근거

ORD 기록
ord-0aa465a90faf45259833d00a44a98cf2
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05621087

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