HCID 57959883, compound → HCID 86635957, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 3-(ethylthio)phenylmagnesium bromide in THF (10 mL 11.6 mmol) was added to a cooled (0° C.) solution of tert-butyl 2-{(Z)-[(tert-butylsulfinyl)imino]methyl}piperidine-1-carboxylate (1.5 g, 4.7 mmol) in THF (10 mL) and the mixture was stirred for 60 min The mixture was quenched with 50 mL of a 1:1 mixture of saturated aqueous ammonium chloride and 33% aqueous ammonia before extracting into ethyl acetate (100 mL). The organic phase was dried (MgSO4) and concentrated. The residue was treated with methanol (20 mL), cooled to 0° C. and then 4N hydrogen chloride in dioxane (5 mL) was added. After stirring for 30 min 4N aqueous sodium hydroxide (6 mL) was added and the mixture was extracted into DCM. The organic extract was dried (Na2SO4) and concentrated. The residue was purified on silica gel eluting with iso-hexane on a gradient of ethyl acetate (0-60%) followed by dichloromethane on a gradient of methanol (2-10%) to give the title product as a 1.7:1 mixture of diastereoisomers (860 mg, 51%). 1H NMR (360 MHz, CDCl3): δ 7.30-7.09 (4H, m), 4.30-4.1 (2H, m), 4.05-3.88 (1H, br), 3.78-3.60 (2H, m), 2.99-2.88 (2H, m), 2.80 (1H, dt, J=2.8, 13.4 Hz), 2.11 (1H, d, J=13.6 Hz), 1.75-1.41 (5H, m), 1.34-1.30 (3H, m), 1.23 (3.5H, s), 1.20 (5.5H, s).

Provenance & Evidence