1,3,5-trimethyl-1H-pyrazole-4-sulfonyl chloride → 2,8-Diazaspiro(4.5)decan-1-one
Reaction equation
C(O)(=O)C.FC(F)(F)OC1C=CC([N:14]2[CH2:18][CH2:17][C:16]3([CH2:23][CH2:22][NH:21][CH2:20][CH2:19]3)[C:15]2=[O:24])=CC=1.CN1C(C)=C(S(Cl)(=O)=O)C(C)=N1>N1C=CC=CC=1>[C:15]1(=[O:24])[C:16]2([CH2:23][CH2:22][NH:21][CH2:20][CH2:19]2)[CH2:17][CH2:18][NH:14]1Participants
4
Procedure
2-(4-Trifluoromethoxy-phenyl)-2,8-diaza-spiro[4.5]decan-1-one acetic acid salt (0.02 g, 0.05 mmol) was dissolved in pyridine (0.5 ml) at room temperature and 1,3,5-trimethyl-1H-pyrazole-4-sulfonyl chloride (0.013 g, 0.06 mmol) was added and the mixture was stirred overnight at room temperature. The reaction mixture was concentrated in vacuo and the resulting residue was dissolved in AcOEt and washed with 0.1M HCl and brine. The organic layer was dried (Na2SO4), filtered and evaporated under reduced pressure to give a crude residue which was purified by flash column chromatography (4:1 AcOEt/heptane) to yield 2-(4-trifluoromethoxy-phenyl)-8-(1,3,5-trimethyl-1H-pyrazole-4-sulfonyl)-2,8-diaza-spiro[4.5]decan-1-onel)-2,8-diaza-spiro[4.5]decan-1-one as an off-white solid (0.09 g, 31%). MS (ESI): 487.3 (MH+)