Potassium Carbonate → HCID 53687753, compound

HRID 2166738Notes

Reaction equation

HRID 2166738 reaction equation
[CH3:1][O:2][C:3]1[C:16]2[C@:15]34[CH2:17][CH2:18][NH:19][C@@H:9]([C@@H:10]3[CH2:11][CH2:12][C:13](=[O:20])[CH2:14]4)[CH2:8][C:7]=2[CH:6]=[CH:5][CH:4]=1.C([O-])([O-])=O.[K+].[K+].[CH:27]1([C:31](Cl)=[O:32])[CH2:30][CH2:29][CH2:28]1>CN(C=O)C>[CH:27]1([C:31]([N:19]2[CH2:18][CH2:17][C@@:15]34[C:16]5[C:3]([O:2][CH3:1])=[CH:4][CH:5]=[CH:6][C:7]=5[CH2:8][C@@H:9]2[C@@H:10]3[CH2:11][CH2:12][C:13](=[O:20])[CH2:14]4)=[O:32])[CH2:30][CH2:29][CH2:28]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 78705Cyclobutanecarbonyl chlorideHCID 22823472HCID 22823472, compound

Product 1

HCID 53687753HCID 53687753, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 2 g (7.37 mmol) 4-methoxymorphinan-6-one (H2O was removed azeotropic) and 3 g (21.71 mmol) K2CO3 in 20 ml dry DMF was dropped at room temperature during 15 min. a solution of 900 mg (7.59 mmol) cyclobutanecarboxylic acid chloride. This mixture was stirred at room temperature for 1 h, then poured on 200 ml ice water and extracted with ether. The organic layer was extracted with 2 N HCl and brine, dried and evaporated to give an oil, which was crystallized with benzene/u/hexane to yield 2.5 g (96%) N-cyclobutylcarbonyl-4-methoxymorphinan-6-one, m.p. 125°-126°, [α]D26 -204.5° (c 0.76, CHCl3).

Workup

  1. extractionextracted with ether
  2. extractionThe organic layer was extracted with 2 N HCl and brine
  3. customdried
  4. customevaporated
  5. customto give an oil, which
  6. customwas crystallized with benzene/u/hexane

Sources & evidence

ORD record
ord-ec3d7d4df4354824b34b0070c661bd75
Source dataset
uspto-grants-1983_06
Patent number
US04388463

Reaction notes

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