(Bis(2-methoxyethyl)amino)sulfur trifluoride → HCID 68505919, compound
Reaction equation
[C:1]([O:5][C:6](=[O:14])[NH:7][CH:8]1[CH2:12][CH2:11][CH:10](O)[CH2:9]1)([CH3:4])([CH3:3])[CH3:2].COCCN(S(F)(F)[F:25])CCOC>C(Cl)Cl>[F:25][C@@H:10]1[CH2:11][CH2:12][C@H:8]([NH:7][C:6](=[O:14])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2])[CH2:9]1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -10 °C
Procedure
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)+.
Workup
- washwashed with sat. aq. NaHCO3 solution
- extractionback-extracted with DCM (3×)
- dry with materialThe collected organic phases were dried (Na2SO4)
- customevaporated under reduced pressure
- customThe crude product was purified by column chromatography on silica gel
Sources & evidence
- ORD record
- ord-b5c45f1c78774f7896733605f4d173e4
- Source dataset
- uspto-grants-2012_09
- Patent number
- US08268827B2
Reaction notes
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