Formic Acid → HCID 59846451, compound

Participants

Reaction Steps

To ice bath-cooled triethylamine (13.3 mL, 95.2 mmol, 7.4 equiv.) was added dropwise formic acid (3.65 mL, 95.2 mmol, 7.4 equiv.). The reaction solution was stirred at RT for 20 min. A solution of (R)-2,2,2-trifluoro-N-(7-fluoro-4-oxo-1,2,3,4-tetrahydronaphthalen-1-yl)acetamide (3.54 g, 12.9 mmol, 1 equiv) in DMF (10 ml) and Noyori catalyst (R,R form) (204.3 mg, 2.5 mol %) were added and stirred at RT overnight. TLC was checked and found only small amount of product formed. The reaction solution was stirred at 40° C. for 16 h. TLC showed reaction completed. The solvents were evaporated off The residue was treated with CH2Cl2 to result a white solid precipitate, which was collected on funnel and washed with small amount of CH2Cl2 (2.15 g). The filtrate gave additional 0.58 g of product after chromatography (ISCO, 30-40% EtOAc-hexane). Total: 2.73 g (77%). 1H NMR (400 MHz, DMSO-d6) δ 9.83 (s, 1H), 7.52 (q, 1H), 7.13 (m, 1H), 6.85 (dd, 1H), 5.36 (d, 1H), 5.05 (m, 1H), 4.55-4.62 (m, 1H), 2.06-2.14 (m, 2H), 1.64-1.80 (m, 2H).

Provenance & Evidence