Benzyl chloroformate → {4-[4-(tert-Butyl-dimethyl-silanyloxy)-cyclohexyl]-2-fluoro-phenyl}-carbamic acid benzyl ester

4-[4-(tert-Butyl-dimethyl-silanyloxy)-cyclohexyl]-2-fluoro-phenylamine (0.85 g, 2.4 mmol) was dissolved in DCM (20 mL). To this solution was transferred a solution of CbzCl (560 mg, 3.28 mmol, 1.3 equiv.) in 5 mL of DCM, followed by addition of powder anhydrous K2CO3 (0.99 g, 7.2 mmol, 3 equiv.). The reaction mixture was stirred at 0° C. to rt. overnight. The reaction was quenched by dilution with DCM (10 mL), followed by addition of NaHCO3 aq. (5 mL). The two layers were separated and the aqueous layer was extracted with DCM (2×5 mL). The combined extracts were washed with NaHCO3 aq. (5 mL), brine (5 mL) and dried (K2CO3). The solution was filtered and the filtrate was concentrated in vacuo to obtain the title compound.

1. customovernight
2. customThe reaction was quenched by dilution with DCM (10 mL)
3. additionfollowed by addition of NaHCO3 aq. (5 mL)
4. customThe two layers were separated
5. extractionthe aqueous layer was extracted with DCM (2×5 mL)
6. washThe combined extracts were washed with NaHCO3 aq. (5 mL), brine (5 mL)
7. dry with materialdried (K2CO3)
8. filtrationThe solution was filtered
9. concentrationthe filtrate was concentrated in vacuo

ORD record

ord-fc11527274d645edabde4dbb35428fd9

Source dataset

uspto-grants-2014_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08735385B2