Sodium borohydride → HCID 178494573, compound

Reaction equation

[CH3:1][O:2][CH2:3][CH:4]1[O:8][C:7](=[O:9])[N:6]([C:10]2[CH:15]=[CH:14][C:13]([CH:16]3[CH2:21][CH2:20][C:19](=[O:22])[CH2:18][CH2:17]3)=[CH:12][N:11]=2)[CH2:5]1.[BH4-].[Na+]>CO.O>[OH:22][C@H:19]1[CH2:20][CH2:21][C@H:16]([C:13]2[CH:14]=[CH:15][C:10]([N:6]3[CH2:5][CH:4]([CH2:3][O:2][CH3:1])[O:8][C:7]3=[O:9])=[N:11][CH:12]=2)[CH2:17][CH2:18]1

Participants

Procedure

A solution of 0.4 g of (RS)-5-methoxymethyl-3-[5-(4-oxo-cyclohexyl)-pyridin-2-yl]-oxazolidin-2-one in 25 ml of methanol and 2.5 ml of water was treated with 0.2 g of sodium borohydride and stirred at room temperature for 16 h. Then, the mixture was concentrated and the residue was taken up in methylene chloride and washed with water. The aqueous phase was extracted with methylene chloride and the organic phases were combined, dried with magnesium sulfate and concentrated. The residue (0.4 g) was recrystallized from ethyl acetate and there was obtained 0.2 g of (RS)-3-[5-(trans-4-hydroxy-cyclohexyl)-pyridin-2-yl]-5-methoxymethyl-oxazolidin-2-one. M.p.: 142°-143°.