8-[(4-Methylbenzene)sulfonyl]-1,4-dioxa-8-azaspiro[4.5]decane synthesis

Yield:853751-19-6 97%

Reaction Conditions:

with triethylamine in diethyl ether;dichloromethane at 20; for 5 h;

Steps:

To a solution of 1,4-dioxa-8-azaspiro[4,5]decane (10.0 g, 70 mmol) and triethylamine (20 mL, 142 mmol) in diethylether (50 mL) cooled to 0° C. was added dropwise tosyl chloride (13.5 g, 71 mmol) dissolved in CH₂Cl₂. The resulting suspension was stirred at room temperature 5 h. and washed with saturated aqueous NaHCO₃, water and dried (Na₂SO₄). Concentration gave the Intermediate 57 as a white solid (20.20 g, 97%). ¹H-NMR (300 MHz, CDCl₃) δ: 7.61 (2H, d, J=8.0 Hz), 7.28 (2H, d, J=8.0 Hz), 3.86 (4H, s), 3.11 (4H, t, J=5.8 Hz), 2.40 (3H, s), 1.75 (4H, t, J=5.8 Hz). LCMS (M+H) calcd for C₁₄H₂₀NO₄S: 298.11; found: 298.16.

References:

US2005/256109,2005,A1 Location in patent:Page/Page column 23