Morpholine → 4-Methanesulfonylmorpholine

Temperature

-20 °C

To a solution of morpholine (2.00 mL, 22.96 mmol) in DCM (40 mL) was added TEA (3.20 mL, 22.96 mmol) at about −20° C., then methanesulfonyl chloride (2.68 mL, 34.4 mmol) was added dropwise at about −20° C. The reaction mixture was stirred at about −20° C. for about 2 h, then warmed to rt. The mixture was partitioned with saturated aqueous NH4Cl (100 mL) and DCM (3×50 mL). The combined organic layers were concentrated and purified by silica gel chromatography eluting with a gradient of 0-100% EtOAc/heptane to give 4-(methylsulfonyl)morpholine (3.95 g, 100%) as a white solid: 1H NMR (DMSO-d6) δ 3.70-3.60 (m, 4H), 3.12-3.04 (m, 4H), 2.89 (s, 3H).

1. temperaturewarmed to rt
2. customThe mixture was partitioned with saturated aqueous NH4Cl (100 mL) and DCM (3×50 mL)
3. concentrationThe combined organic layers were concentrated
4. custompurified by silica gel chromatography
5. washeluting with a gradient of 0-100% EtOAc/heptane

ORD record

ord-78abb3b6024d49568a98d24a25d6a0fa

Source dataset

uspto-grants-2013_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08426411B2