Triethylamine → HCID 57027097, compound

HRID 372156Notes

Reaction equation

HRID 372156 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[CH2:7][C@H:8]3[NH:19][CH2:18][CH2:17][C@@:14]4([C:15]=2[CH:16]=1)[C@@:9]3([OH:21])[CH2:10][CH2:11][C:12](=[O:20])[CH2:13]4.C(N(CC)CC)C.[CH:29]1([C:33](Cl)=[O:34])[CH2:32][CH2:31][CH2:30]1>C1C=CC=CC=1>[CH:29]1([C:33]([N:19]2[CH2:18][CH2:17][C@@:14]34[C:15]5[CH:16]=[C:3]([O:2][CH3:1])[CH:4]=[CH:5][C:6]=5[CH2:7][C@@H:8]2[C@:9]3([OH:21])[CH2:10][CH2:11][C:12](=[O:20])[CH2:13]4)=[O:34])[CH2:32][CH2:31][CH2:30]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 78705Cyclobutanecarbonyl chlorideHCID 57040061HCID 57040061, compound

Product 1

HCID 57027097HCID 57027097, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

In an anhydrous system 32 g of 3-methoxy-14-hydroxy-6-ketomorphinan, 16 ml triethylamine and 300 ml of benzene are stirred together and, over a 30 minute period, a solution of 13 g of cyclobutylcarbonylchloride in 100 ml of benzene is added. The internal temperature is kept below 25° by means of an ice bath, after which stirring is continued for four more hours at room temperature. In the isolation, triethylaminehydrochloride is removed by filtration, the solvent evaporated, and the residue solidified by stirring in 200 ml of petroleum ether to give crude N-cyclobutylcarbonyl-3-methoxy-14-hydroxy-6-ketomorphinan.

Workup

  1. customThe internal temperature is kept below 25° by means of an ice bath
  2. customis continued for four more hours at room temperature
  3. customIn the isolation, triethylaminehydrochloride is removed by filtration
  4. customthe solvent evaporated
  5. stirringby stirring in 200 ml of petroleum ether

Sources & evidence

ORD record
ord-87b57ef1e8e74487a0812c4f8ffa5b9d
Source dataset
uspto-grants-1978_05
Patent number
US04089855

Reaction notes

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