Water → HCID 86609960, compound

Participants

Reaction Conditions

Reaction Steps

nButyl lithium (1.6M in hexanes) (31.3 mL, 50 mmol) was added dropwise to N-(1,1,3,3-tetramethyl-butyl)-methanesulfonamide (5.23 g, 25 mmol) in tetrahydrofuran (30 mL) at −78° C. under an atmosphere of nitrogen. The mixture was warmed to 0° C. for 30 minutes then cooled to −78° C. 3-Pyridine carboxaldehyde (2.4 mL, 25 mmol) in tetrahydrofuran (20 mL) was added dropwise to the mixture over 20 minutes and the mixture was warmed to room temperature and stirred for a further 1 hour. Water (100 mL) was added to the reaction mixture and the whole was extracted with ethyl acetate (2×100 mL). The combined organics were dried over MgSO4, filtered and concentrated in vacuo to afford a pale yellow solid. The solid was washed with dichloromethane (10 mL) in heptane (100 mL) to afford 2-hydroxy-2-pyridin-3-yl-ethanesulfonic acid (1,1,3,3-tetramethyl-butyl)-amide as a pale yellow solid (5.67 g, 72%).

Provenance & Evidence