Benzyl chloroformate → HCID 54152127, compound

A solution of 3-fluoro-4-(3-methoxy-1-azetidinyl)nitrobenzene (1.50 g, 6.64 mmol) in 1:1 methanol/tetrahydrofuran (35 mL) was treated with 10% palladium on carbon and then ammonium formate (1.26 g, 19.9 mmol) at room temperature. After 20 min the color of the reaction mixture changed from yellow to colorless. The reaction mixture was filtered through Celite® and the filtrate concentrated under reduced pressure. The recovered oil was immediately dissolved in 3:1 acetone/water (25 mL) and treated with potassium carbonate (2.75 g, 19,9 mmol) and benzyl chloroformate (1.31 mL, 8.30 mmol). After 30 min TLC analysis (6% acetonitrile/chloroform) revealed the reaction to be complete. The reaction mixture was extracted with chloroform (3×20 mL). The combined organic extracts were washed with brine, dried over sodium sulfate, filtered and concentrated in vacuo to a purple oil. This material was chromatographed over silica gel (100 g), eluting with a gradient of 1-3% acetonitrile/chloroform, to give, after concentration of appropriate fractions, 1.24 g (56%) of the title compound as an off-white solid with mp 95°-96.5° C. and MS(EI) 330 (M+).

1. customat room temperature
2. filtrationThe reaction mixture was filtered through Celite®
3. concentrationthe filtrate concentrated under reduced pressure
4. dissolutionThe recovered oil was immediately dissolved in 3:1 acetone/water (25 mL)
5. customthe reaction
6. extractionThe reaction mixture was extracted with chloroform (3×20 mL)
7. washThe combined organic extracts were washed with brine
8. dry with materialdried over sodium sulfate
9. filtrationfiltered
10. concentrationconcentrated in vacuo to a purple oil
11. customThis material was chromatographed over silica gel (100 g)
12. washeluting with a gradient of 1-3% acetonitrile/chloroform
13. customto give

ORD record

ord-9328082edaa24b2ebfdcefe7931d722b

Source dataset

uspto-grants-1999_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05883093