Methyl 6-aminonicotinate → (6-Aminopyridin-3-yl)methanol

To a cold (0° C.) mixture of 6-Aminonicotinic acid methyl ester (0.511 g, 3.36 mmol) and Cerium(III) chloride heptahydrate (1.25 g, 3.36) in dry THF was slowly added lithium borohydride (8.4 mL, 1 M in THF) over a 30 minute period. The mixture was allowed to warm to room temperature overnight then slowly quenched by the addition of ice water (20 mL). After stirring for 1 hr the mixture was filtered through Celite diluted with EtOAc (30 mL) and layers were separated. The aqueous layer was further extracted with EtOAc (1×). The combined EtOAc extracts were washed with brine, dried over MgSO4, evaporated in vacuo and provide a crude semi-solid. The white solid product was triturated with diethyl ether, filtered and dried under reduced pressure.

1. customover a 30 minute
2. customthen slowly quenched by the addition of ice water (20 mL)
3. filtrationwas filtered through Celite
4. additiondiluted with EtOAc (30 mL) and layers
5. customwere separated
6. extractionThe aqueous layer was further extracted with EtOAc (1×)
7. washThe combined EtOAc extracts were washed with brine
8. dry with materialdried over MgSO4
9. customevaporated in vacuo
10. customprovide a crude semi-solid
11. customThe white solid product was triturated with diethyl ether
12. filtrationfiltered
13. customdried under reduced pressure

ORD record

ord-7e7a44d42d3b4070a6f7816e1c89f627

Source dataset

uspto-grants-2014_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08796313B2