Chlorotrimethylsilane → HCID 68592696, compound

Participants

Reaction Conditions

Reaction Steps

Compound 6.2 (2.2 g, 7.14 mmol) was dissolved in 30 mL pyridine and cooled to 0° C. To this was added TMSCl (2.7 mL, 21.4 mmol). The mixture was stirred at 0° C. for 30 min and then treated with BzCl (4.95 mL, 35.7 mmol). The mixture was stirred at 0° C. for 3 h and then treated with NH4OH (7.3 mL), stirred at 0° C. for another 30 min. The mixture was concentrated under reduced pressure and the residue was partitioned between CH2Cl2 and 1N HCl. The water layer was extracted three times with CH2Cl2. The organic layer was combined, dried over MgSO4, filtered and concentrated under reduced pressure. The residue was subjected to a silica gel column chromatography eluting with 80% EtOAc in Hexane to yield compound 6.3 (1.84 g, 63% yield). 1HNMR (300 MHz, CDCl3) δ 1.42 (s, 3H), 1.70 (s, 3H), 3.79-4.01 (m, 2H), 4.63 (s, 1H), 5.14-5.16 (m, 1H), 5.31-5.35 (m, 1H), 6.68 (d, 1H, J=4.2), 7.55-7.61 (m, 2H), 7.61-7.69 (m, 1H), 8.08 (d, 2H, J=7.2), 8.90 (s, 1H). LRMS (ESI) MH+ C19H20N6O5 requires 413.2. Found 412.9.

Provenance & Evidence