(Bis(2-methoxyethyl)amino)sulfur trifluoride → HCID 68505919, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (3-hydroxycyclopentyl)-carbamic acid tert-butyl ester (prepared as described in Tetrahedron 1999, 55, 10815-10834) (1 eq) in DCM (1 M) at −10° C. was added [bis(2-methoxyethyl)amino]sulfur trifluoride (1 eq). The reaction mixture was stirred at −10° C. for 15 min, then the reaction mixture was diluted with DCM, washed with sat. aq. NaHCO3 solution, and back-extracted with DCM (3×). The collected organic phases were dried (Na2SO4), and evaporated under reduced pressure. The crude product was purified by column chromatography on silica gel to afford tert-butyl cis-3-fluorocyclopentylcarbamate, MS (ES) C10H18FNO2 requires: 203 found: 204 (M+H)+. A solution of this intermediate in DCM/TFA (1:1, 0.24 M) was stirred at RT for 30 min and then concentrated under reduced pressure. The resulting crude was used as such in the next step without further purification. MS (ES) C5H10FN requires: 103 found: 104 (M+H)+.

Provenance & Evidence