1-methyl-2,3-dihydro-1H-imidazol-2-one → 1-[(1R,2S)-2-(2,4-difluorophenyl)-2,3-epoxy-1-methylpropyl]-3-methyl-2(1H,3H)-imidazolone

HRID 129116Notes

Reaction equation

HRID 129116 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C@:9]1([C@@H:12](O)[CH3:13])[CH2:11][O:10]1.[CH3:15][N:16]1[CH:20]=[CH:19][NH:18][C:17]1=[O:21]>>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C@:9]1([O:10][CH2:11]1)[C@H:12]([N:18]1[CH:19]=[CH:20][N:16]([CH3:15])[C:17]1=[O:21])[CH3:13]

Participants

3

Reactant 2

HCID 5665891-methyl-2,3-dihydro-1H-imidazol-2-oneHCID 10631861(1S)-[(2R)-(2,4-difluorophenyl)-2-oxiranyl]ethanol

Product 1

HCID 572115651-[(1R,2S)-2-(2,4-difluorophenyl)-2,3-epoxy-1-methylpropyl]-3-methyl-2(1H,3H)-imidazoloneYield 17.2%

Procedure

In the same manner as in Reference Example 5, starting from 423 mg of (1S)-1-[(2R)-2-(2,4-difluorophenyl)-2oxiranyl]ethanol and 207 mg of 1-methyl-2(1H,3H)-imidazolone prepared by a method described in Journal of American Chemical Society vol. 98, page 8218 (1976), 102 mg of 1-[(1R,2S)-2-(2,4-difluorophenyl)-2,3-epoxy-1-methylpropyl]-3-methyl-2(1H,3H)-imidazolone was obtained as a colorless oil.

Workup

  1. customprepared by a method

Sources & evidence

ORD record
ord-8d95000e0b4d496ab3718c516de7e5b2
Source dataset
uspto-grants-1995_11
Patent number
US05466820

Reaction notes

Loading…