Lithium borohydride → N-[6-chloro-4-(hydroxymethyl)pyridin-2-yl]-N-propylmethanesulfonamide
Reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([N:12]([S:16]([CH3:19])(=[O:18])=[O:17])[CH2:13][CH2:14][CH3:15])[N:11]=1)[C:5](OC)=[O:6].[BH4-].[Li+]>C1COCC1>[Cl:1][C:2]1[N:11]=[C:10]([N:12]([CH2:13][CH2:14][CH3:15])[S:16]([CH3:19])(=[O:17])=[O:18])[CH:9]=[C:4]([CH2:5][OH:6])[CH:3]=1Participants
4
Procedure
To a solution of methyl 2-chloro-6-[(methylsulfonyl)(propyl)amino]isonicotinate (3.52 g, 11.47 mmol) in THF (50 mL), cooled to 0° C., was added lithium borohydride (17.3 mL, 34.4 mmol, 2M THF) slowly via serynge. The reaction mixture was allowed to warm to RT by itself and stirred at RT for 3 h. The reaction mixture was carefully quenched with EtOAc, MeOH and water sequentially. The reaction mixture was diluted with EtOAc, the organic layer was separated, dried over sodium sulfate and concentrated in vacuo to give N-[6-chloro-4(hydroxymethyl)pyridin-2-yl]-N-propylmethanesulfonamide as a yellow thick oil. 1H NMR (400 MHz, CDCl3) δ 7.27 (s, 1H), 7.23 (s, 1H), 4.72 (s, 2H), 3.80 (t, J=8 Hz, 2H), 3.00 (s, 3H), 2.02 (s, 1H), 1.59-1.46 (m, 2H), 0.90 (t, J=7.6 Hz, 3H).