Potassium Sodium Tartrate → tert-Butyl [(2R)-1-hydroxy-4-(methylsulfanyl)butan-2-yl]carbamate

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Reaction Steps

A solution of N-(tert-butoxycarbonyl)-D-methionine (12.47 g, 50 mmol) and sodium bis(2-methoxyethoxy)aluminum hydride (Red-Al®) (50 mmol) in dry toluene (125 mL) was stirred at 0° C. for 30 minutes, then at ambient temperature for 1 hour. The mixture was treated with aqueous Rochelle salt and extracted with diethyl ether. The extract was washed sequentially with brine and aqueous NaHCO3, dried (MgSO4), filtered, and concentrated to provide the desired product (9.05 g).

Provenance & Evidence