tert-Butylsulfinamide, (R)-(+)- → HCID 12995921, compound

Participants

Reaction Steps

(R)-2-Methylpropane-2-sulfinamide (25) (8.63 g, 71.3 mmol) and Ti(OEt)4 (30 mL, 142.6 mmol) were added to a solution of cyclopropylcarboxaldehyde (24) (5 g, 71.3 mmol) in THF (142 mL). The reaction mixture was stirred at rt for 17 h after which brine (142 mL) was added and the resulting suspension was filtered through a pad of Celite. The filtrate was extracted with EtOAc (200 mL) and the organic phase was dried (Na2SO4), filtered and concentrated under vacuum to give 12.7 g (quant) of (R,E)-N-(cyclopropylmethylene)-2-methylpropane-2-sulfinamide (26). Retention time (min)=1.459 method [1], MS (m/z) 174.1 (M+H)+.

Provenance & Evidence