Sodium Carbonate → HCID 70567185, compound

HRID 1680232Notes

Reaction equation

HRID 1680232 reaction equation
Cl.[CH3:2][O:3][C:4]1[CH:5]=[CH:6][C:7]2[CH2:8][C@H:9]3[NH:20][CH2:19][CH2:18][C@@:15]4([C:16]=2[CH:17]=1)[C@@:10]3([O:23][CH3:24])[C@H:11]([CH3:22])[CH2:12][C:13](=[O:21])[CH2:14]4.[CH:25]1([CH2:28]Br)[CH2:27][CH2:26]1.C(=O)([O-])[O-].[Na+].[Na+]>C(O)C>[CH:25]1([CH2:28][N:20]2[CH2:19][CH2:18][C@@:15]34[C:16]5[CH:17]=[C:4]([O:3][CH3:2])[CH:5]=[CH:6][C:7]=5[CH2:8][C@@H:9]2[C@:10]3([O:23][CH3:24])[C@H:11]([CH3:22])[CH2:12][C:13](=[O:21])[CH2:14]4)[CH2:27][CH2:26]1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 81503BromomethylcyclopropaneHCID 70567811HCID 70567811, compound

Product 1

HCID 70567185HCID 70567185, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 3,14-dimethoxy-8α-methylmorphinan-6-one hydrochloride (26) (0.83 g, 2.36 mmol), cyclopropylmethyl bromide (0.51 g 3.78 mmol), anhydrous sodium carbonate (1.6 g, 15.09 mmol) and ethanol (20 ml) was refluxed at oil bath temperature of 110° C. for 18 hours with stirring under a nitrogen atmosphere. The resulting product was filtered and the residue washed with ethanol (3×35 ml). The filtrate was concentrated under reduced pressure give 0.689 g of a solid product which was purified by chromatography on silica gel using graded methanol/chloroform mixtures to provide 0.362 g (41.5% theory) of 17-cyclopropylmethyl-3,14-dimethoxy-8α-methylmorphinan-6-one (30) as a tan foamy solid.

Workup

  1. filtrationThe resulting product was filtered
  2. washthe residue washed with ethanol (3×35 ml)
  3. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-78e0605f6ab94acbadb669c068776a0d
Source dataset
uspto-grants-1981_06
Patent number
US04272540

Reaction notes

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