Methyl iodide → tert-Butyl (S)-5-(methylsulfanyl)-3,4-dihydro-2H-pyrrole-2-carboxylate

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Reaction Steps

To a solution of (S)-pyrrolidin-2-thione-5-carboxylic acid t-butyl ester (1.75 g, 8.71 mmol) in 35 mL of dry THF was added MeI (2.2 mL, 34.83 mmol) at rt. The mixture was stirred at rt for 3 h and concentrated under vacuum. CH2Cl2 was added to the resulting oil which was poured into a sat. solution of NaHCO3. This was extracted 3 times with CH2Cl2, dried over MgSO4, and concentrated to provide (S)-2-methylsulfanyl-3,4-dihydro-5H-pyrrole-5-carboxylic acid t-butyl ester (1.63 g, 87%) as a brown oil which was used without further purification 1H NMR (CDCl3) δ 1.46 (s, 9H), 2.09 (m, 1H), 2.28 (m, 1H), 2.48 (s, 3H), 2.56-2.80 (m, 2H), 4.59 (m, 1H). MS calcd for C10H17NO2S+H, 216, found 216.

Provenance & Evidence