Cyclopropanecarboxaldehyde → HCID 86679002, compound

Participants

Reaction Steps

To the intermediate from Step B (20 mg, 0.045 mmol) in MeOH (45.2 μl) and DCM (45.2 μl) was added cyclopropanecarbaldehyde (3.17 mg, 0.045 mmol) followed by sodium triacetoxyborohydride (28.7 mg, 0.136 mmol). The reaction was stirred for 3 h at room temperature and was quenched with aqueous NaHCO3. The solution was extracted with EtOAc. The organic layer was dried (sodium sulfate), concentrated in vacuo and purified by silica gel column chromatography to afford the title product as a white solid. 1H NMR (500 MHz, CHCl3-d): δ 9.20 (s, 1H); 8.77 (d, J=8.07 Hz, 1H); 8.56 (dd, J=4.53, 1.58 Hz, 1H); 7.13 (dd, J=8.08, 4.50 Hz, 1H); 5.55 (s, 2H); 4.95-4.88 (m, 3H); 2.88-2.74 (m, 2H); 2.27 (dd, J=11.46, 6.00 Hz, 1H); 2.20-1.94 (m, 1H); 1.54 (s, 3H); 0.87-0.80 (m, 1H); 0.48-0.37 (m, 2H); 0.05-0.00 (m, 2H). m/z=497.1 (M+H).

Provenance & Evidence