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

反応式

HRID 53867 の反応式
[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]

参加物

5

反応物 3

HCID 3283Diethyl EtherHCID 7918Acetic AnhydrideHCID 5288826Morphine

生成物 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]ethanone収率 80%

試薬・触媒・溶媒 1

HCID 516892Sodium Bicarbonate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-0aa465a90faf45259833d00a44a98cf2
出典データセット
uspto-grants-1997_04
特許番号
US05621087

関連ノート

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