Sodium borohydride → HCID 5148089, compound

To a solution of 2 (133 g, 0.54 mol) in methanol (1000 ml) and water (200 ml) was added sodium borohydride (41 g, 1.08 mol) in portions at temperatures below 28° C. After the addition the mixture was stirred for 1 hour at room temperature. Most of the methanol was distilled off. To the residue was added saturated ammonium chloride solution (200 ml), and the mixture was extracted three times with ether (300 ml). The combined organic phases were washed once with water and were then extracted three times with 4M hydrochloric acid (300 ml). The colored aqueous phases were kept for 1 hour at room temperature, and pH was then adjusted to 14. The mixture was extracted three times with ether (250 ml), and the combined organic phases were separated from the solid byproducts. The organic phase was washed with 4 portions of saturated sodium chloride solution (200 ml), dried over magnesium sulphate and evaporated. This yielded 17.4 g (0.143 mol, 26%) of crude oily title compound, which was sufficiently pure according to the 1H NMR spectrum.

1. additionAfter the addition the mixture
2. distillationMost of the methanol was distilled off
3. additionTo the residue was added saturated ammonium chloride solution (200 ml)
4. extractionthe mixture was extracted three times with ether (300 ml)
5. washThe combined organic phases were washed once with water
6. extractionwere then extracted three times with 4M hydrochloric acid (300 ml)
7. waitThe colored aqueous phases were kept for 1 hour at room temperature
8. extractionThe mixture was extracted three times with ether (250 ml)
9. customthe combined organic phases were separated from the solid byproducts
10. washThe organic phase was washed with 4 portions of saturated sodium chloride solution (200 ml)
11. dry with materialdried over magnesium sulphate
12. customevaporated

ORD record

ord-af116897d8064514954fb7273017dacb

Source dataset

uspto-grants-1990_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04925858