[CH3:1][C:2]1[N:3]=[C:4]([C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][CH:13]=2)[S:5][C:6]=1[CH:7]([OH:11])[CH2:8][CH:9]=[CH2:10].[OH2:22].[OH-].[Na+].OO>O1CCCC1.C(OCC)(=O)C>[CH3:1][C:2]1[N:3]=[C:4]([C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:19])[F:20])=[CH:14][CH:13]=2)[S:5][C:6]=1[CH:7]([OH:11])[CH2:8][CH2:9][CH2:10][OH:22]To a solution of [rac]-1-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-yl]-but-3-en-1-ol [200 mg, 0.64 mmol; PCT Int. Appl. (2002), WO 02/062774 A1] in tetrahydrofuran (2 ml) was added a 1 M solution of borane-tetrahydrofuran complex in tetrahydrofuran (1.28 ml, 1.28 mmol) at ambient temperature under an argon atmosphere. The yellow solution was stirred for 1 h, water (1 ml), 3 M aqueous NaOH solution (0.2 ml) and 35% aqueous H2O2 solution (0.2 ml) were added and stirring was continued for 1 h. Water and ethyl acetate were added, the layers were separated and the aqueous layer was extracted with ethyl acetate. The combined organic layers were washed two times with brine and dried over sodium sulfate. The solvent was removed under reduced pressure to give 212 mg (0.64 mmol, quant.) of the title compound which was used in the next step without further purification.
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