Chlorotrimethylsilane → HCID 67437266, Verbindung

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-Eintrag

ord-f736bc4da247459a986a74b5907f985c

Quelldatensatz

uspto-grants-2012_12

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08329709B2