Triethylamine → HCID 13100609, compound

HRID 1758507Notes

Reaction equation

HRID 1758507 reaction equation
[CH:1]1[C:14]2[CH2:13][C@H:12]3[NH:15][CH2:16][CH2:17][C@:6]4([C@H:11]3[CH2:10][CH2:9][CH2:8][CH2:7]4)[C:5]=2[CH:4]=[C:3]([C:18](=[O:20])[CH3:19])[CH:2]=1.C(N(CC)CC)C.[O:28]1[CH:32]=[CH:31][CH:30]=[C:29]1[CH2:33][C:34](Cl)=[O:35]>C(Cl)Cl>[C:18]([C:3]1[CH:2]=[CH:1][C:14]2[CH2:13][C@H:12]3[N:15]([C:34]([CH2:33][C:29]4[O:28][CH:32]=[CH:31][CH:30]=4)=[O:35])[CH2:16][CH2:17][C@@:6]4([C:5]=2[CH:4]=1)[C@H:11]3[CH2:10][CH2:9][CH2:8][CH2:7]4)(=[O:20])[CH3:19]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 75975Furan-2-acetyl chlorideHCID 13100586HCID 13100586, compound

Product 1

HCID 13100609HCID 13100609, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of 1.5 g, (-)-1-(morphinan-3-yl)ethanone, 1.7 g of triethylamine and 15 ml of methylene chloride at ice-bath temperature was added a solution of 1.3 g of 2-furyl acetyl chloride in 10 ml of methylene chloride over a period of 1 hour. After the mixture had been refluxed for 4 hours, it was cooled to room temperature and the solvent was removed under reduced pressure. The residue was dissolved in 100 ml ether and the ether solution was washed with 1 N hydrochloric acid (2×15 ml) then with water and dried over magnesium sulfate. Removal of the solvent gave 1.9 g (90%) of crude (-)-3-acetyl-N-[(2-furylmethyl)carbonyl]morphinan. For analysis, a sample of this compound was distilled, bp 235°-245° (0.05 mm), [α]25D-160.43° (c 0.94, MeOH).

Workup

  1. temperatureAfter the mixture had been refluxed for 4 hours
  2. customthe solvent was removed under reduced pressure
  3. dissolutionThe residue was dissolved in 100 ml ether
  4. washthe ether solution was washed with 1 N hydrochloric acid (2×15 ml)
  5. dry with materialwith water and dried over magnesium sulfate
  6. customRemoval of the solvent

Sources & evidence

ORD record
ord-bb96ddb74fe74f2db290d19e18e690df
Source dataset
uspto-grants-1983_02
Patent number
US04374139

Reaction notes

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