Lithium Hydroxide → 6-{[(2S)-2-methoxypropyl]oxy}nicotinic acid
Reaction equation
Cl[C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8]CC)=[O:7])=[CH:4][N:3]=1.[CH3:13][O:14][C@@H:15]([CH3:18])[CH2:16][OH:17].[OH-].[Li+]>>[CH3:13][O:14][C@@H:15]([CH3:18])[CH2:16][O:17][C:2]1[CH:12]=[CH:11][C:5]([C:6]([OH:8])=[O:7])=[CH:4][N:3]=1Participants
4
Conditions
- Temperature
- 75 °C
Procedure
The title compound was synthesized as described for Intermediate example I-81 in 67% yield starting from ethyl 6-chloronicotinate and (s)-(+)-2-methoxypropanol. The reduction was performed using 3 equiv of lithium hydroxide while heating to 75° C. for 3 h. The final aqueous solution was extracted with ethyl acetate in order to collect the product; 1H NMR (400 MHz, CD3OD) δ ppm 8.77 (d, 1 H), 8.21 (dd, 1 H), 6.87 (d, 1 H), 4.27-4.40 (m, 2 H), 3.69-3.81 (m, 1 H), 3.42 (s, 3 H), 1.24 (d, 3 H); MS (ESI) m/z 212[M+H+], m/z 210 [M−H+].