Methanol → HCID 69880792, 화합물

반응식

CO[C:3]1([S:9]([C:11]2[CH:12]=[C:13]([CH:15]=[CH:16][CH:17]=2)[NH2:14])=[O:10])[CH:8]=[CH:7][CH:6]=[CH:5][CH2:4]1.[N:18]1[CH:23]=[CH:22][CH:21]=[C:20]([CH:24]=O)[CH:19]=1.[BH4-].[Na+].[CH3:28][OH:29]>>[CH3:28][O:29][C:8]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:9]([C:11]1[CH:12]=[C:13]([NH:14][CH2:24][C:20]2[CH:19]=[N:18][CH:23]=[CH:22][CH:21]=2)[CH:15]=[CH:16][CH:17]=1)=[O:10]

참가 물질

반응물 4

HCID 887Methanol

HCID 103713-Pyridinecarboxaldehyde

HCID 4311764Sodium borohydride

HCID 69881808HCID 69881808, 화합물

생성물 1

HCID 69880792HCID 69880792, 화합물수율 82%

실험 절차

3-(1-Methoxyphenylsulfinyl)aniline (145 mg, 0.59 mmol) and pyridine-3-carboxaldehyde (63 mg, 0.59 mmol) were reacted in anhydrous methanol (3.0 ml), followed by treatment with sodium borohydride (44 mg, 1.17 mmol) as previously described (Intermediate 3). Silica gel chromatography (2 mm Chromatotron® plate, eluting with 20/1 ethyl acetate/hexanes) afforded N-(3-(2-methoxyphenylsulfinyl)phenyl)pyrid-3-ylmethylamine (162 mg, 82%) as an oil. 1H NMR(400 MHz): 3.77(3H,s), 4.35(2H,br s), 6.61(1H,m), 6.83(1H,d,J=8.0), 6.96(1H,br t), 7.01-7.04(1H,m), 7.11(1H,dt,J=7.8, 1.0), 7.18(1H,t,J=7.8), 7.21-7.28(1H,br s), 7.35-7.41(1H,m), 7.63(1H,br d), 7.82(2H,dd,J=7.8, 1.5), 8.40-8.80(2H,br s); MS(ESI)m/z 339.1([M+H]+,100)