Sodium borohydride → (4-(2-Fluorophenyl)-1-methyl-1H-1,2,3-triazol-5-yl)methanol

To a stirred solution of 4-(2-Fluorophenyl)-1-methyl-1H-1,2,3-triazole-5-carbaldehyde 4 (38 g, 185.19 mmol) under nitrogen atmosphere in methanol (300 ml) was added sodium borohydride (8.407 g, 222.23 mmol) in portion wise at 0° C. and the reaction mass stirred for 20 min. The reaction was monitored by TLC and UPLC. The reaction mixture was quenched with water (500 ml) and concentrated to remove methanol and water. Then it was extracted with ethyl acetate (4×500 ml), combined organic layer was washed with brine (50 ml), dried over sodium sulphate, filtered and concentrated to afford crude mass (34 g, 88.6% mass balance). The above solid was triturated with hexane (3×100 ml), the supernant layer was decanted and the solid was dried to afford desired product (4-(2-Fluorophenyl)-1-methyl-1H-1,2,3-triazole-5-yl) methanol (31 g, 80.77%) as off-white solid.

1. customThe reaction mixture was quenched with water (500 ml)
2. concentrationconcentrated
3. customto remove methanol and water
4. extractionThen it was extracted with ethyl acetate (4×500 ml)
5. washwas washed with brine (50 ml)
6. dry with materialdried over sodium sulphate
7. filtrationfiltered
8. concentrationconcentrated
9. customto afford crude mass (34 g, 88.6% mass balance)
10. customThe above solid was triturated with hexane (3×100 ml)
11. customthe supernant layer was decanted
12. customthe solid was dried

ORD-Eintrag

ord-00d6430ebd5a4b9ca4b2d92d562ab3a7

Quelldatensatz

uspto-grants-2015_12

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09206160B2