HCID 15453674, compound → HCID 54114465, compound

A 1000 mL 3-neck round bottom flask fitted with a mechanical stirrer, reflux condenser, addition port, and nitrogen inlet was charged with a 1.0 M solution of lithium aluminum hydride (200 mL) in THF and anhydrous THF (200 mL). The solution was cooled in an ice/water bath and 2(R)-amino-3-(4-fluorobenzylsulfanyl)-propionic acid (24.08 g) was added with rapid stirring in small portions over 15 min. The ice bath was removed and the reaction mixture was heated to reflux overnight. After cooling the reaction mixture to room temperature, saturated aqueous potassium carbonate (50 mL) was added dropwise over 1 h. The solids were filtered off and the filter cake was washed with THF. The combined filtrate was dried over anhydrous MgSO4 and concentrated to give 2(R)-amino-3-(4-fluoro-benzylsulfanyl)-propan-1-ol (16.16 g) as a pale amber resin.

1. customA 1000 mL 3-neck round bottom flask fitted with a mechanical stirrer
2. temperaturereflux condenser
3. additionaddition port, and nitrogen inlet
4. temperatureThe solution was cooled in an ice/water bath
5. customThe ice bath was removed
6. temperaturethe reaction mixture was heated
7. temperatureto reflux overnight
8. additionsaturated aqueous potassium carbonate (50 mL) was added dropwise over 1 h
9. filtrationThe solids were filtered off
10. washthe filter cake was washed with THF
11. dry with materialThe combined filtrate was dried over anhydrous MgSO4
12. concentrationconcentrated

ORD record

ord-41de5668dfbe43ecbdb3b742ee43b21b

Source dataset

uspto-grants-2009_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07547701B2