Allyl bromide → HCID 22823466, compound

HRID 2166736Notes

Reaction equation

HRID 2166736 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+].[CH2:27](Br)[CH:28]=[CH2:29]>CN(C=O)C>[CH2:29]([N:19]1[CH2:18][CH2:17][C@@:15]23[C:16]4[C:3]([O:2][CH3:1])=[CH:4][CH:5]=[CH:6][C:7]=4[CH2:8][C@@H:9]1[C@@H:10]2[CH2:11][CH2:12][C:13](=[O:20])[CH2:14]3)[CH:28]=[CH2:27]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 22823472HCID 22823472, compound

Product 1

HCID 22823466HCID 22823466, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 700 mg (2.44 mmol) 4-methoxymorphinan-6-one.1H2O, 900 mg (6.51 mmol) anhydrous K2CO3 and 310 mg (2.56 mmol) allyl bromide in 20 ml dry DMF was stirred at 80° C. for 30 min. Then the mixture was cooled to room temperature, filtered, and the filtrate evaporated in vacuo. The resulting oil was partitioned between water and ether, the organic layer washed with brine, dried and evaporated to give an oil which was crystallized with u-hexanes. To 700 mg (93%) N-allyl-4-methoxymorphinan-6-one, m.p. 84°-86°, [α]D26 -114.6° (c 0.79, CHCl3), were obtained.

Workup

  1. filtrationfiltered
  2. customthe filtrate evaporated in vacuo
  3. customThe resulting oil was partitioned between water and ether
  4. washthe organic layer washed with brine
  5. customdried
  6. customevaporated
  7. customto give an oil which
  8. customwas crystallized with u-hexanes

Sources & evidence

ORD record
ord-50e940fc9ea94eceb424983cf233d7fe
Source dataset
uspto-grants-1983_06
Patent number
US04388463

Reaction notes

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