Methylamine → HCID 118098712, compound

Participants

Reaction Steps

To a solution of 11B (0.965 g, 4.00 mmol) in MeOH (20 mL) was added methylamine (33% in EtOH) (0.598 mL, 4.80 mmol). The mixture was stirred at rt for 1.5 h, then was cooled to 0° C. sodium borohydride (0.182 g, 4.80 mmol) was added, then the mixture was stirred at rt for 1 h, then was concentrated. The resultant residue was taken up in THF (20 mL) and was treated with sat. NaHCO3 (10 mL). The mixture was stirred at rt for 10 min, then was treated with Boc2O (1.048 g, 4.80 mmol). The mixture was stirred at rt for 2 h. The THF was removed in vacuo, then the aqueous phase was extracted with EtOAc. The organic phase was washed with H2O and brine, dried (Na2SO4) and concentrated. The crude product was purified by flash chromatography (loaded in chloroform onto a 80 g column and eluted with a gradient from 0 to 50% ethyl acetate/hexanes) to give 11C (1.05 g, 2.95 mmol, 73.6% yield) as an yellow oil. MS (ESI) m/z: 379.1 [M+Na]+; 1H NMR (400 MHz, chloroform-d) δ ppm 7.78-7.94 (2H, m), 4.57 (2H, br. s.), 2.90 (3H, s), 2.49 (1H, qd, J=7.2, 4.3 Hz), 1.38-1.53 (9H, m), 0.92-0.98 (2H, m), 0.62-0.68 (2H, m).

Provenance & Evidence