Cyclopropanecarbonyl chloride → HCID 53861772, compound

HRID 261104Notes

Reaction equation

HRID 261104 reaction equation
[O:1]([C:8]1[CH:9]=[CH:10][C:11]2[CH2:12][C@H:13]3[N:24](C)[CH2:23][CH2:22][C@@:19]4([C:20]=2[CH:21]=1)[C@H:14]3[CH2:15][CH2:16][CH2:17][CH2:18]4)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:26]1([C:29](Cl)=[O:30])[CH2:28][CH2:27]1>C1(C)C=CC=CC=1>[O:1]([C:8]1[CH:9]=[CH:10][C:11]2[CH2:12][C@H:13]3[N:24]([C:29]([CH:26]4[CH2:28][CH2:27]4)=[O:30])[CH2:23][CH2:22][C@@:19]4([C:20]=2[CH:21]=1)[C@H:14]3[CH2:15][CH2:16][CH2:17][CH2:18]4)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 77637Cyclopropanecarbonyl chlorideHCID 15942836HCID 15942836, compound

Product 1

HCID 53861772HCID 53861772, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

To a solution of 3.7 g (0.011 mol) of (-)-3-phenoxy-N-methylmorphinan in 50 ml of toluene, 5.8 g of cyclopropane carboxylic acid chloride in 25 ml of toluene was added dropwise at 5°. The mixture was allowed to warm to room temperature and was then refluxed for 15 hours. The solvent was removed in vacuo and the residue partitioned between ether and dilute hydrochloric acid. The ether solution was washed with water and dried. Removal of the solvent in vacuo afforded 4.2 g (99%) of (-)-3-phenoxy-N-cyclopropylcarbonylmorphinan. For analysis, a sample of this compound was distilled, bp 230°-240°/0.05 mmHg, [α]25D-173.45° (c 0.99, MeOH).

Workup

  1. temperaturewas then refluxed for 15 hours
  2. customThe solvent was removed in vacuo
  3. customthe residue partitioned between ether and dilute hydrochloric acid
  4. washThe ether solution was washed with water
  5. customdried
  6. customRemoval of the solvent in vacuo

Sources & evidence

ORD record
ord-67f6e4e756374dc2977ab3c4412e65b2
Source dataset
uspto-grants-1979_08
Patent number
US04163853

Reaction notes

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