Chlorotrimethylsilane → HCID 67437266, compound

A solution of lithium tetrahydroborate (190 mg, 8.50 mmol) in THF (4 mL) was cooled to 0° C. Chlorotrimethylsilane (2.2 mL, 17 mmol) was added dropwise. The mixture was stirred for 20 minutes at room temperature and then returned to 0° C. (S)-2-amino-3-(2,4-dichlorophenyl)propanoic acid (1.00 g, 4.27 mmol) was then added. The reaction was allowed to warm up slowly to room temperature while stirring overnight. The mixture was cooled to 0° C. and quenched by slow addition of methanol (1 mL) followed by an aqueous solution of 2N sodium hydroxide (4.2 mL, 8.54 mmol). Volatiles were removed under reduces pressure. The slurry was diluted with water (5 mL) and extracted with DCM (3×15 mL). The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated to afford (S)-2-amino-3-(2,4-dichlorophenyl)propan-1-ol as a solid that was used in the next step without further purification. MS m/z 220 (M+).

1. customreturned to 0° C.
2. additionwas then added
3. temperatureto warm up slowly to room temperature
4. stirringwhile stirring overnight
5. temperatureThe mixture was cooled to 0° C.
6. customquenched by slow addition of methanol (1 mL)
7. customVolatiles were removed
8. additionThe slurry was diluted with water (5 mL)
9. extractionextracted with DCM (3×15 mL)
10. washThe combined organic layers were washed with brine
11. dry with materialdried over Na2SO4
12. filtrationfiltered
13. concentrationconcentrated

ORD record

ord-f229933c84fb4c528e491551e3719c1c

Source dataset

uspto-grants-2016_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09328091B2