Methyl 2-(hydroxymethyl)nicotinate

Uses

Methyl 2-(hydroxymethyl)nicotinate can be used as pharmaceutical intermediate for laboratory research.

Description

Methyl 2-(hydroxymethyl)nicotinate is a derivative of methyl nicotinate, which is used in the preparation of a novel glycosidase inhibitor, 1-azasugars. Methyl 2-(hydroxymethyl)nicotinate and its derivatives are used in the preparation of haemoglobin modulators^[1].

Synthesis

To a solution of methyl 2-(acetoxymethyl)nicotinate (7.90 g, 37.76 mmol, 1.0 equiv), in MeOH (80 mL) was added acetyl chloride (3.60 g, 45.86 mmol, 1.2 equiv). The reaction solution was stirred overnight at room temperature; then, the solvent was removed under reduced pressure, and the resulting residue was dissolved in water (20 mL). The pH was adjusted to 8 with NaHCO 3 solid and extracted with ethyl acetate (30 mL*3). The combined organic phase was dried over anhydrous sodium sulfate and filtered, and the filtrate was concentrated in vacuum. The residue was puri - fied by silica gel column with ethyl acetate/petroleum ether (1/1), giving Methyl 2-(hydroxymethyl)nicotinate. LCMS (ES) [M+1] + m/z: 168.

References

[1] GUOHUA ZHAO; Bruce G; Urmila C Deo. Selective Fowler Reductions: Asymmetric Total Syntheses of Isofagomine and Other 1-Azasugars from Methyl Nicotinate[J]. Organic Letters, 2000. DOI:10.1021/ol006810x.