Réaction #1552108

Équation de réaction

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

Solvants

ethanol

Conditions de réaction

Traitement

1. 1
   workup.STIRRINGthe reaction stirred for 12 hours
2. 2
   AutreThe solvent is removed by evaporation
3. 3
   workup.DISSOLUTIONthe residue dissolved in methanol (5 mL)
4. 4
   Autrepurified via prep HPLC
5. 5
   Lavageeluting with water/acetonitrile

Mode opératoire

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.

Source