Sodium borohydride → 4-Piperidinemethanol, 4-(phenylamino)-1-(2-phenylethyl)-

반응식

[BH4-].[Na+].[C:3]1([NH:9][C:10]2([CH:24]=[O:25])[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH2:12][CH2:11]2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1>CO.O>[C:3]1([NH:9][C:10]2([CH2:24][OH:25])[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH2:12][CH2:11]2)[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

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실험 절차

Sodium borohydride (2 g) was added portionwise to a stirred solution of 4-(N-phenylamino)-1-(2-phenylethyl)piperidine-4-carboxaldehyde (2 g) in methanol (2 g) at room temperature for 2 hours. The mixture was diluted with water, extracted with chloroform and the combined extracts washed, dried over MgSO4 and concentrated. The residue was chromatographed on silica gel, using chloroform-methanol 19:1 as eluant, to afford 4-(N-phenylamino)-1-(2-phenylethyl)-4-piperidinylmethanol (1.65 g), m.p. 98°-99° C.