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

Reaction equation

HRID 53867 reaction equation
[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]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 7918Acetic AnhydrideHCID 5288826Morphine

Product 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]ethanoneYield 80%

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-0aa465a90faf45259833d00a44a98cf2
Source dataset
uspto-grants-1997_04
Patent number
US05621087

Linked notes

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