Dimethyldioxirane → 1-Hydroxy-2,6-diphenyl-4-piperidone 1,2-Hexadecylene Ketal

HRID 2254394Notes

Reaction equation

HRID 2254394 reaction equation
[CH2:1]1[O:36][C:18]2([CH2:23][CH:22]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[NH:21][CH:20]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[CH2:19]2)[O:17][CH:2]1[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].CC1(C)O[O:39]1>C(O)C>[CH2:1]1[O:36][C:18]2([CH2:23][CH:22]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[N:21]([OH:39])[CH:20]([C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=3)[CH2:19]2)[O:17][CH:2]1[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

Participants

4

Reactant 2

HCID 115197DimethyldioxiraneHCID 867471002,6-Diphenyl-4-piperidone 1,2-Hexadecylene Ketal

Product 1

HCID 867471011-Hydroxy-2,6-diphenyl-4-piperidone 1,2-Hexadecylene KetalYield 65%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The general procedure of Example 2 is repeated using 10.9 g (22.2 mmol) of 2,6-diphenyl-4-piperidone 1,2-hexadecylene ketal and 376 mL (22.2 mmol) of dimethyldioxirane (0.059M in acetone). 7.3 g (65% yield) of the title compound is isolated as a white solid by recrystallization from ethanol: mp 98°-100° C.

Sources & evidence

ORD record
ord-76c8d419e1384fdfac140a67c9cba29d
Source dataset
uspto-grants-1993_08
Patent number
US05235056

Reaction notes

Loading…