Water → HCID 53984372, compound

HRID 2166737Notes

Reaction equation

HRID 2166737 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[CH:11]=[CH:12][C:13](=[O:20])[CH2:14]4)[CH2:8][C:7]=2[CH:6]=[CH:5][CH:4]=1.O.C([O-])([O-])=O.[K+].[K+].[CH:28]1([C:31](Cl)=[O:32])[CH2:30][CH2:29]1>CN(C=O)C>[CH:28]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]1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 77637Cyclopropanecarbonyl chlorideHCID 86738926HCID 86738926, compound

Product 1

HCID 53984372HCID 53984372, compoundYield 85.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a mixture of 1.5 g (5.18 mmol) 4-methoxymorphinen-6-one.1 H2O, 1.3 g (9.41 mmol) anhydrous K2CO3 and 10 ml dry DMF were added dropwise a solution of 0.29 ml (5.31 mmol) cyclopropanecarboxylic acid chloride in 5 ml dry DMF during 10 min. at room temperature. This mixture was stirred at room temperature for 1 h, then poured on 50 ml ice water and extracted with ether. The organic layer was extracted with 2 N HCl, water and brine, dried and evaporated to give an oil, which was crystallized with ether/n-hexane. To 1.5 g (85%) N-cyclopropylcarbonyl-4-methoxymorphinan-6-one, m.p. 144°-147°, [α]D26 -210.0° (c 1.04, CHCl3), were obtained.

Workup

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

Sources & evidence

ORD record
ord-af00b1ba26644718a95bb9e8653424f0
Source dataset
uspto-grants-1983_06
Patent number
US04388463

Reaction notes

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