Chlorotrimethylsilane → HCID 61056428, compound

Temperature

0 °C

To a stirred 2 M LiBH4 solution (16.22 ml) at r.t. in THF under an argon atmosphere was added chlorotrimethylsilane (5.47 ml) over 2 min. The white suspension was cooled to 0° C. and (RS)-(2-amino-2-(2,4-difluoro-phenyl)-propionic acid hydrochloride (2.57 g) was added portionwise over 5 min. The ice bath was removed and the compact off-white suspension was stirred at r.t. for 20 h. The mixture was cooled again to 0° C. and treated carefully with methanol (15 ml). The mixture was stirred at r.t. for 30 min, filtered and the cake was washed with MeOH. The filtrate was concentrated. The crude product was purified by column chromatography (silica gel; gradient: CH2Cl2->CH2Cl2/MeOH 9:1) to give (RS)-2-amino-2-(2,4-difluoro-phenyl)-propan-1-ol (1.47 g, 73%) as colorless viscous oil.

1. customThe ice bath was removed
2. temperatureThe mixture was cooled again to 0° C.
3. additiontreated carefully with methanol (15 ml)
4. stirringThe mixture was stirred at r.t. for 30 min
5. filtrationfiltered
6. washthe cake was washed with MeOH
7. concentrationThe filtrate was concentrated
8. customThe crude product was purified by column chromatography (silica gel; gradient: CH2Cl2->CH2Cl2/MeOH 9:1)

ORD record

ord-2d9383f2c1a7408dab3467d66fb1aac8

Source dataset

uspto-grants-2013_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08604061B2