Methanol → 1-(5-(Hydroxymethyl)-4-methylthiazol-2-yl)-3-(4-(trifluoromethyl)benzyl)imidazolidin-2-one
Reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([N:12]2[CH2:16][CH2:15][N:14]([CH2:17][C:18]3[CH:23]=[CH:22][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:20][CH:19]=3)[C:13]2=[O:28])[S:5][C:6]=1[C:7](OCC)=[O:8].[BH4-].[Li+].CO>>[OH:8][CH2:7][C:6]1[S:5][C:4]([N:12]2[CH2:16][CH2:15][N:14]([CH2:17][C:18]3[CH:19]=[CH:20][C:21]([C:24]([F:25])([F:27])[F:26])=[CH:22][CH:23]=3)[C:13]2=[O:28])=[N:3][C:2]=1[CH3:1]Participants
Procedure
To a solution of ethyl 4-methyl-2-(2-oxo-3-(4-(trifluoromethyl)benzyl)-imidazolidin-1-yl)thiazole-5-carboxylate (1.00 g, 2.41 mmol) in tetrahedrofuran (50 mL) was added lithium borohydride (2.7 mL of 2.0 M solution in tetrahedrofuran, 5.4 mmol) and methanol (0.10 mL, 2.47 mmol). The reaction mixture was stirred for 22 hours at ambient temperature and quenched with water. The resulting solution was extracted with chloroform and washed with water. The organic solution was dried over anhydrous sodium sulfate, filtered and concentrated in vacuo, and the residue was purified by column chromatography to afford the title compound in 56% yield (0.51 g): mp 153-154° C. (ethyl acetate/hexanes); 1H NMR (300 MHz, DMSO-d6) δ 7.59 (d, J=8.1 Hz, 2H), 7.40 (d, J=8.1 Hz, 2H), 4.69 (d, J=5.1 Hz, 2H), 4.52 (s, 2H), 4.13-4.02 (m, 2H), 3.45-3.40 (m, 2H), 2.26 (s, 3H); MS (ES+) m/z 372.1 (M+1).
Workup
- customquenched with water
- extractionThe resulting solution was extracted with chloroform
- washwashed with water
- dry with materialThe organic solution was dried over anhydrous sodium sulfate
- filtrationfiltered
- concentrationconcentrated in vacuo
- customthe residue was purified by column chromatography
Sources & evidence
- ORD record
- ord-2215c9a6646f4756b64da6ecbf5c3e8e
- Source dataset
- uspto-grants-2012_10
- Patent number
- US08293768B2
Reaction notes
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