Potassium Carbonate → HCID 13145946, compound

HRID 2166944Notes

Reaction equation

HRID 2166944 reaction equation
[OH:1][C@:2]12[C@@H:15]3[NH:16][CH2:17][CH2:18][C@:7]1([C:8]1[C:9]([O:19][CH3:20])=[CH:10][CH:11]=[CH:12][C:13]=1[CH2:14]3)[CH2:6][C:5](=[O:21])[CH2:4][CH2:3]2.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:16]2[CH2:17][CH2:18][C@@:7]34[C:8]5[C:9]([O:19][CH3:20])=[CH:10][CH:11]=[CH:12][C:13]=5[CH2:14][C@@H:15]2[C@:2]3([OH:1])[CH2:3][CH2:4][C:5](=[O:21])[CH2:6]4)=[O:32])[CH2:30][CH2:29]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 77637Cyclopropanecarbonyl chlorideHCID 13145942HCID 13145942, compound

Product 1

HCID 13145946HCID 13145946, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To an ice-cooled mixture of 330 mg (1.15 mmol) 14-hydroxy-4-methoxymorphinan-6-one, 400 mg (2.89 mmol) anhydrous K2CO3 in 10 ml dry DMF was dropped a solution of 0.11 ml (1.21 mmol) cyclopropanecarboxylic acid chloride in 3 ml dry DMF during 10 min. while stirring. This mixture was stirred at 0° C. for an additional 50 min., then filtered, washed with CHCl3 and the filtrate evaporated. The residue was partitioned between water and CH2Cl2, the organic layer separated, washed with brine, dried and evaporated. The resulting solid residue was crystallized with ethanol to give 350 mg (86%) N-cyclopropylcarbonyl-14-hydroxy-4-methoxymorphinan-6-one, m.p. 223°-225°, [α]D26 --167.2° (C 0.97, CHCl3).

Workup

  1. stirringThis mixture was stirred at 0° C. for an additional 50 min.
  2. filtrationfiltered
  3. washwashed with CHCl3
  4. customthe filtrate evaporated
  5. customThe residue was partitioned between water and CH2Cl2
  6. customthe organic layer separated
  7. washwashed with brine
  8. customdried
  9. customevaporated
  10. customThe resulting solid residue was crystallized with ethanol

Sources & evidence

ORD record
ord-8fc21f53554841119a988c56c96cf359
Source dataset
uspto-grants-1983_06
Patent number
US04390699

Reaction notes

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