Formic Acid → HCID 68115412, compound

Participants

Reaction Conditions

Reaction Steps

To a 25-mL round-bottom flask containing a solution of 16.5 (100 mg, 0.23 mmol, 1.00 equiv) in methanol (5 mL) was added HCHO (37%, 1 mL) and HCOOH (5 mL) at room temperature under nitrogen. The resulting solution was stirred overnight at 100° C. and evaporated under reduced pressure. The crude product (80 mg) was purified by preparative HPLC(SHIMADZU) under the following conditions: column: SunFire Prep C18, 19*150 mm 5 um; mobile phase: water (0.05% NH4HCO3) and CH3CN (start at 7.0% CH3CN then ramp up to 63.0% in 13 min); UV detection at 254 and 220 nm. The product-containing fractions were collected and the solvents evaporated to afford Compound I-33 (8 mg) as a colorless oil. An ee of 100% was measured by chiral-SFC analysis. 1H NMR (300 MHz, CDCl3) δ 7.26 (s, 1H), 5.24 (m, 1H), 3.72 (t, 1H), 3.47 (m, 1H), 3.08 (m, 2H), 2.70 (m, 1H), 2.03-2.68 (m, 11H), 1.25-1.81 (m, 9H). MS: m/z 362 (M+H)+.

Provenance & Evidence