Methyl 6-(hydroxymethyl)nicotinate synthesis
- Product Name:Methyl 6-(hydroxymethyl)nicotinate
- CAS Number:56026-36-9
- Molecular formula:C8H9NO3
- Molecular Weight:167.16
881-86-7
178 suppliers
$28.00/1g
56026-36-9
188 suppliers
$9.00/100mg
Yield:56026-36-9 96%
Reaction Conditions:
Stage #1:dimethyl 2,5-pyridine dicarboxylate with calcium chloride in tetrahydrofuran;ethanol for 0.5 h;
Stage #2: with sodium tetrahydroborate;ethanol in tetrahydrofuran at 0;
Steps:
10.1
Step 1. Synthesis of methyl 6-(hydroxymethyl)nicotinate (55):A mixture of dimethyl pyridine-2,5-dicarboxylate (54; 100.0 g, 0.51 mol), CaCl2 (227.4 g, 2.05 mol), THF (1100 mL) and EtOH (1200 mL) was stirred for 30 min, NaBH4 (48.6 g, 1.28 mol) was added portionwise at 0ºC. The mixture was stirred for 18 hours. Saturated NH4Cl solution (1.5 L) and water (2.0L) was added slowly, and the resulting mixture was extracted with dichloromethane (3 x 3.0 L). The combined organic solvent was dried over MgSO4 and concentrated to give methyl 6- (hydroxymethyl)nicotinate 55 (82.0 g, 96%).
References:
SIRTRIS PHARMACEUTICALS, INC.;NARAYAN, Radha;DISCH, Jeremy, S.;PERNI, Robert, B.;VU, Chi, B. WO2010/56549, 2010, A1 Location in patent:Page/Page column 103
63362-34-5
16 suppliers
$594.00/1g
56026-36-9
188 suppliers
$9.00/100mg
49668-89-5
6 suppliers
$176.72/250mgs:
56026-36-9
188 suppliers
$9.00/100mg
100-26-5
367 suppliers
$8.00/5g
56026-36-9
188 suppliers
$9.00/100mg
5470-70-2
537 suppliers
$5.00/5g
56026-36-9
188 suppliers
$9.00/100mg