Borane;tetrahydrofuran → HCID 57150513, compound

Borane-tetrahydrofuran complex (1 M in tetrahydrofuran, 60 mL, 60 mmol) was added at 0° C. to a suspension of O-benzyl-L-homoserine (5.06 g, 24.1 mmol) in tetrahydrofuran (100 mL). The ice bath was removed, and the reaction mixture was stirred for 72 h at room temperature, then the reaction was stopped by careful addition of methanol (40 mL). After evaporation of volatile material, the residue was taken up in 5% methanolic sulfuric acid solution (50 mL). The solution was heated at reflux for 2 h, then concentrated in vacuo. The residue was partitioned between ethyl acetate and 1 M aq. sodium hydroxide solution, the aqueous layer was saturated with sodium chloride and extracted with ethyl acetate three times. The combined organic phases were dried (MgSO4), filtered, and evaporated to afford the title compound (5.02 g), which was directly used in the next step. Colorless oil, MS (ISP)=196.1 (M+H)+.

1. customThe ice bath was removed
2. additionthe reaction was stopped by careful addition of methanol (40 mL)
3. customAfter evaporation of volatile material
4. temperatureThe solution was heated
5. temperatureat reflux for 2 h
6. concentrationconcentrated in vacuo
7. customThe residue was partitioned between ethyl acetate and 1 M aq. sodium hydroxide solution
8. extractionextracted with ethyl acetate three times
9. dry with materialThe combined organic phases were dried (MgSO4)
10. filtrationfiltered
11. customevaporated

ORD record

ord-b9b3d7394e7048c2b7ef7fd6570258cd

Source dataset

uspto-grants-2011_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08071586B2