Ethyl Acetate → 2-(1-((Tert-butoxy)carbonyl)-3-hydroxyazetidin-3-yl)acetic acid

Participants

Reaction Conditions

Reaction Steps

LHMDS (6.43 mL of 1N solution in THF) was cooled to −78° C. Ethyl acetate (0.63 mL, 6.43 mmol) was added and the reaction mixture was stirred for 10 minutes. tert-Butyl 3-oxoazetidine-1-carboxylate (1 g, 5.84 mmol) was added to the mixture and the reaction was stirred for 15 minutes. The reaction mixture was warmed to 0° C. and was then quenched with water (25 mL). The reaction mixture was extracted with ether. The organic phase was dried over anhydrous magnesium sulfate, filtered and concentrated. The remaining oil was dissolved in MeOH (25 mL) and 1N NaOH (15 mL) was added and the mixture was stirred at room temperature overnight. This was concentrated in vacuo to remove MeOH and then to the remaining aqueous solution was added 1N HCl (100 mL). This mixture was extracted with CH2Cl2 (100 mL). The organic phase was dried over anhydrous magnesium sulfate, filtered and concentrated to afford the title intermediate (215 mg) as an oil.

Provenance & Evidence