Benzyl chloroformate → HCID 87288030, compound

To a solution of pivaldehyde (1.00 mL, 0.00921 mol) in DCM (30 mL) was added 2,2-diethoxy-ethanamine, (1.35 mL, 0.00921 mol) followed by sodium triacetoxyborohydride (2.15 g, 0.0101 mol). The reaction mixture was stirred at room temperature for 1 h and then DIPEA (1.43 g, 0.0110) mol) was added. The reaction mixture was cooled to 0° C., and benzyl chloroformate (1.88 g, 0.0110 mol) was added dropwise. The reaction mixture was stirred for 1 h, concentrated, and 6 M TFA in water (20 mL) was added. The reaction mixture was stirred for 2 h and the TFA was removed under vacuum. The resulting aqueous solution was diluted with saturated NaCl (15 mL) The product was extracted with ethyl acetate (25 mL. The organic layer was collected, dried over anhydrous sodium sulfate, filtered, and concentrated. The crude product was purified by flash column chromatography eluting with 10-20% ethyl acetate in hexanes to give an oil (2.2 g) which was further purified by flash column chromatography to give the title compound as a yellow oil (0.72 g).

1. temperatureThe reaction mixture was cooled to 0° C.
2. stirringThe reaction mixture was stirred for 1 h
3. concentrationconcentrated
4. addition6 M TFA in water (20 mL) was added
5. stirringThe reaction mixture was stirred for 2 h
6. customthe TFA was removed under vacuum
7. additionThe resulting aqueous solution was diluted with saturated NaCl (15 mL) The product
8. extractionwas extracted with ethyl acetate (25 mL
9. customThe organic layer was collected
10. dry with materialdried over anhydrous sodium sulfate
11. filtrationfiltered
12. concentrationconcentrated
13. customThe crude product was purified by flash column chromatography
14. washeluting with 10-20% ethyl acetate in hexanes

ORD record

ord-3b552501831948e6bb237b7c7ffa8dc7

Source dataset

uspto-grants-2014_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08802698B2