tert-Butylsulfinamide, (R)-(+)- → tert-butyl N-[(1S)-1-(4-bromophenyl)ethyl]-N-[(3Z)-3-tert-butylsulfanylimino-3-phenylpropyl]carbamate

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Reaction Steps

A mixture of (S)-tert-butyl 1-(4-bromophenyl)ethyl(3-oxo-3-phenylpropyl)carbamate (30 g, 0.069 mol), (R)-2-methylpropane-2-sulfinamide (8.42 g, 0.069 mol), and Ti(i-OPr)4 (31.4 g, 0.138 mol) in THF (300 mL) was heated to reflux overnight. The mixture was treated with brine, and the precipitate was filtered. The filtrate was concentrated to give (S,Z)-tert-butyl 1-(4-bromophenyl)ethyl(3-(tert-butylthioimino)-3-phenylpropyl)carbamate (20 g, 55%) which was used in the next step without further purification. 1H NMR (CDCl3): δ=1.23 (s, 9H), 1.32 (s, 9H), 1.46 (d, 3H), 1.70-1.86 (m, 2H), 3.24-3.75 (m, 2H), 4.08 (m, 1H), 7.09-7.91 (m, 9H).

Provenance & Evidence