反応 #1552108

反応方程式

1-(4′-Methylbenzenesulfonyl)-3-hydroxypyridin-2(1H)-one

formaldehyde

Pyrrolidine

→

desired product

1-(4′-Methylbenzenesulfonyl)-3-hydroxy-4-(pyrrolidin-1-ylmethyl)pyridin-2(1H)-one

溶媒

ethanol

反応条件

後処理

1. 1
   workup.STIRRINGthe reaction stirred for 12 hours
2. 2
   その他The solvent is removed by evaporation
3. 3
   workup.DISSOLUTIONthe residue dissolved in methanol (5 mL)
4. 4
   その他purified via prep HPLC
5. 5
   洗浄eluting with water/acetonitrile

実験手順

1-(4′-Methylbenzenesulfonyl)-3-hydroxypyridin-2(1H)-one (7) (250 mg, 0.94 mmol) and formaldehyde (200 mg, 2.07 mmol) are combined in aqueous ethanol (10 mL) and stirred for 30 minutes. Pyrrolidine (149 mg, 2.07 mmol) is then added and the reaction stirred for 12 hours. The solvent is removed by evaporation and the residue dissolved in methanol (5 mL) and purified via prep HPLC eluting with water/acetonitrile to afford the desired product. 1H NMR (300 MHz, DMSO) δ 1.87 (m, 2H), 1.99 (m, 2H), 2.44 (s, 3H), 3.09 (m, 2H), 3.40 (m, 2H), 4.19 (s, 2H), 6.51 (d, J=7.5 Hz, 1H), 7.51 (d, J=8.4 Hz, 1H), 7.76 (d, J=7.5 Hz, 1H), 7.98 (d, J=8.1 Hz, 1H), 9.93 (broad s, 1H); 19F NMR (252 MHz, DMSO) δ 88.4; 13C NMR (75 MHz, DMSO) δ 21.5, 22.7, 50.5, 53.7, 108.7, 118.6, 119.4, 128.4, 129.7, 130.1, 133.1, 146.8, 147.7, 156.2; ES MS (M+1) 349.25; HRMS Calcd. For C17H20N2O4S, 348.42. Found (M+1) 349.42.

出典