Imidazole → HCID 53934734, compound

HRID 975638Notes

Reaction equation

[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.CC(C)([O-])C.[K+].[CH2:12]([O:15][C:16]([N:18]1[CH2:22][C@H:21]([O:23][Si:24]([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:26])[CH3:25])[CH2:20][C@H:19]1[CH2:31][CH2:32][CH2:33]OS(C)(=O)=O)=[O:17])[CH:13]=[CH2:14].O>CN(C)C=O>[CH2:12]([O:15][C:16]([N:18]1[CH2:22][C@H:21]([O:23][Si:24]([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:25])[CH3:26])[CH2:20][C@H:19]1[CH2:31][CH2:32][CH2:33][N:1]1[CH:5]=[CH:4][N:3]=[CH:2]1)=[O:17])[CH:13]=[CH2:14]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of imidazole (3.57 g) in dimethylformamide (100 ml) was added potassium t-butoxide (5.89 g) portionwise at room temperature and the mixture was stirred at the same temperature for 10 minutes. Then a solution of (2R,4R)-1-allyloxycarbonyl-4-t-butyldimethylsilyloxy-2-(3-methanesulfonyloxypropyl)pyrrolidine (20.1 g), in dimethylformamide (20 ml) was added and the mixture was heated at 60° C. After stirring for 1 hour, water (200 ml) was added and the mixture was extracted with hexane-ethyl acetate (2:1) (200 ml×5). The combined extract was washed with water (1 l), brine (1 l), and dried over magnesium sulfate. Evaporation of the solvent gave (2R,4R)-1-allyloxycarbonyl-4-t-butyldimethylsilyloxy-2-[3-(imidazol-1-yl)propyl]pyrrolidine (18.1 g) as a yellow paste.

Workup

stirringAfter stirring for 1 hour
extractionthe mixture was extracted with hexane-ethyl acetate (2:1) (200 ml×5)
extractionThe combined extract
washwas washed with water (1 l), brine (1 l)
dry with materialdried over magnesium sulfate
customEvaporation of the solvent

Sources & evidence

ORD record: ord-c2a0cb7ab19a4437a1761949797dafa6
Source dataset: uspto-grants-1997_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05608056

Reaction notes

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