反应详情

A mixture of 3-(methylamino)methylazetidine-1-carboxylic acid tert-butyl ester (450 mg, 2.25 mmol), oxetan-3-one (135 mg, 1.88 mmol), in dichloromethane (10 mL) was stirred at RT for 1.5 h. Sodium triacetoxyborohydride (797 mg, 3.76 mmol) was added and the resulting reaction mixture was stirred at RT under nitrogen atmosphere for 18 h. The mixture was diluted with water, the phases were separated and the aqueous phase was extracted with EtOAc (2×25 mL). The combined organic layers were dried over sodium sulfate, filtered and the solvents reduced in vacuo The residue was purified by column chromatography (Si—PPC, MeOH:DCM, gradient 0:100 to 5:95) to afford the title compound as a colourless oil (330 mg, 69%). 1H NMR (400 MHz, CDCl3): δ 4.64 (2H, t, J=6.58 Hz), 4.57 (2H, t, J=6.26 Hz), 4.01 (2H, t, J=8.40 Hz), 3.57-3.55 (3H, m), 2.71-2.61 (1H, m), 2.41 (2H, d, J=7.57 Hz), 2.08 (3H, s), 1.44 (9H, s).

1. customthe resulting reaction mixture
2. customthe phases were separated
3. extractionthe aqueous phase was extracted with EtOAc (2×25 mL)
4. dry with materialThe combined organic layers were dried over sodium sulfate
5. filtrationfiltered
6. customwas purified by column chromatography (Si—PPC, MeOH:DCM, gradient 0:100 to 5:95)