反应详情

温度

90 °C

Under argon atmosphere, [(3-bromo-2-fluorobenzyl)oxy](tert-butyl)dimethylsilane (5.5 g), 3-[(benzyloxy)methyl]azetidine (2.5 g), and toluene (50 ml) were mixed, and (1E,4E)-1,5-diphenylpenta-1,4-dien-3-one palladium (3:2) (900 mg), BINAP (1.8 g), and sodium tert-butoxide (2.5 g) were added thereto, followed by stirring at 90° C. for 3 hours. The reaction mixture was cooled to room temperature, and EtOAc were added thereto, followed by filtering using Celite as a filtration adjuvant. The filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (hexane/EtOAc). The purified product thus obtained was mixed with EtOH (40 ml), and 10% palladium carbon (1 g) was added thereto, followed by stirring at room temperature overnight under hydrogen atmosphere of 1 atm and filtering using Celite as a filtration adjuvant. The filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (CHCl3/MeOH) to obtain {1-[3-({[tert-butyl(dimethyl)silyl]oxy}methyl)-2-fluorophenyl]azetidin-3-yl}methanol (885 mg).

1. temperatureThe reaction mixture was cooled to room temperature
2. filtrationby filtering
3. concentrationThe filtrate was concentrated under reduced pressure
4. customthe residue was purified by silica gel column chromatography (hexane/EtOAc)
5. customThe purified product thus obtained
6. additionwas added
7. stirringby stirring at room temperature overnight under hydrogen atmosphere of 1 atm
8. filtrationfiltering
9. concentrationThe filtrate was concentrated under reduced pressure
10. customThe residue was purified by silica gel column chromatography (CHCl3/MeOH)