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

HRID 1758505Notes

Reaction equation

HRID 1758505 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-fd72a3eb433e4cdca7b00a1df87b90f1
Source dataset
uspto-grants-1983_02
Patent number
US04374139

Reaction notes

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