Potassium Carbonate → HCID 13145938, compound

HRID 2166942Notes

Reaction equation

HRID 2166942 reaction equation
O[C:2]1([O:22][CH3:23])[C:15]2[C@:14]34[CH2:16][CH2:17][N:18]([CH3:19])[C@@H:8]([C@:9]3([OH:21])[CH2:10][CH2:11][C:12](=[O:20])[CH2:13]4)[CH2:7][C:6]=2[CH:5]=[CH:4][CH2:3]1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.[Cl-].C1([N+](C)(C)C)C=CC=CC=1>[OH:21][C@:9]12[C@@H:8]3[N:18]([CH3:19])[CH2:17][CH2:16][C@:14]1([C:15]1[C:2]([O:22][CH3:23])=[CH:3][CH:4]=[CH:5][C:6]=1[CH2:7]3)[CH2:13][C:12](=[O:20])[CH2:11][CH2:10]2

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 70533263HCID 70533263, compound

Product 1

HCID 13145938HCID 13145938, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 67309Phenyltrimethylammonium chlorideCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 2.2 g (7.66 mmol) 4,14-dihydroxy-4-methoxy-N-methylmorphinan-6-one in 50 ml dry DMF were added 2.12 g (15.34 mmol) anhydrous K2CO3 and 3.96 g (23.07 mmol) phenyltrimethylammonium chloride and this mixture was stirred at 90° C. (bath temperature) for 4 h. After cooling to room temperature, the mixture was filtered, washed with CHCl3 and evaporated (90° C. bath temperature). The residue was partitioned between ethyl acetate and water, the organic layer separated and washed with water, dried and evaporated to give 2.1 g of a crystalline residue. After recrystallization with ethanol 1.78 g (77%) of 14-hydroxy-4-methoxy-N-methylmorphinan-6-one, m.p. 191°-193°, [α]D26 --83.9° (C 0.88, CHCl3) were obtained.

Workup

  1. temperatureAfter cooling to room temperature
  2. filtrationthe mixture was filtered
  3. washwashed with CHCl3
  4. customevaporated (90° C. bath temperature)
  5. customThe residue was partitioned between ethyl acetate and water
  6. customthe organic layer separated
  7. washwashed with water
  8. customdried
  9. customevaporated

Sources & evidence

ORD record
ord-4b3a3bb66c06415fb87eb00e070de11e
Source dataset
uspto-grants-1983_06
Patent number
US04390699

Reaction notes

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