tert-Butylsulfinamide, (S)-(-)- → Benzyl 5-{[(S)-tert-butylsulfinyl]imino}-2,2-dimethylpentanoate

Participants

Reaction Steps

To a mixture of benzyl 2,2-dimethyl-5-oxopentanoate (1.06 g, 4.54 mmol, Step C) and anhydrous CuSO4 (1.59 g, 9.98 mmol) in DCM (10 mL) was added (S)-2-methylpropane-2-sulfinamide (0.550 g, 4.54 mmol). This mixture was stirred for 22 hours, before being filtered through a pad of celite. Additional DCM was used to wash the celite. The combined organics were concentrated in vacuo to give a residue that was purified by silica gel chromatography, eluting with a gradient of MeOH:DCM—0.5:99.5 to 1.5:98.5, to give the title compound. MS: m/z=338 (M+1).

Provenance & Evidence