(Bis(2-methoxyethyl)amino)sulfur trifluoride → tert-Butyl 3-(4-cyanophenyl)-3-fluoroazetidine-1-carboxylate

HRID 1487905Notes

Reaction equation

[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2(O)[CH2:12][N:11]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:10]2)=[CH:5][CH:4]=1)#[N:2].COCCN(S(F)(F)[F:31])CCOC>ClCCl>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2([F:31])[CH2:12][N:11]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:10]2)=[CH:5][CH:4]=1)#[N:2]

Participants

Conditions

Temperature: -78 °C

Procedure

Into a 250-mL 3-necked round-bottom flask, purged and maintained with an inert atmosphere of nitrogen, was placed a solution of tert-butyl 3-(4-cyanophenyl)-3-hydroxyazetidine-1-carboxylate (compound 43.2, 5.00 g, 18.2 mmol) in dichloromethane (120 mL). The solution was cooled to −78° C. and Deoxo-Fluor® (bis(2-methoxyethyl)aminosulfur trifluoride) (5.99 g, 27.1 mmol) was added drop-wise. The resulting mixture was stirred for 1.5 h at −78° C., then carefully quenched with sodium bicarbonate (50 mL, 1 M). The organic layer was additionally washed with brine (2×50 mL), dried (Na2SO4), filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography with ethyl acetate/petroleum ether (1/50-1/30) as the eluent to yield 3.2 g (64%) of the title compound as colorless oil.

Workup

customInto a 250-mL 3-necked round-bottom flask, purged
temperaturemaintained with an inert atmosphere of nitrogen
customcarefully quenched with sodium bicarbonate (50 mL, 1 M)
washThe organic layer was additionally washed with brine (2×50 mL)
dry with materialdried (Na2SO4)
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe residue was purified by silica gel column chromatography with ethyl acetate/petroleum ether (1/50-1/30) as the eluent

Sources & evidence

ORD record: ord-55ef0b5adec944bb92c12e0464933e32
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09428502B2

Reaction notes

Loading…