tert-butyl (2S,4S)-4-amino-2-(hydroxymethyl)pyrrolidine-1-carboxylate

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Heat a mixture of (2S,4S)-4-amino-2-hydroxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester (0.14 mol, 31 g), 5-bromo-2-fluoronitrobenzene (0.29 mol, 64.0 g) and triethylamine (0.58 mol, 59 g) in ethyl acetate (320 mL) to reflux for 16 h. Cool the reaction mixture to room temperature, dilute with ethyl acetate, and wash with water and brine. Dry the organic layer over anhydrous sodium sulfate, filter, and concentrate to obtain the title compound (42 g, crude) as a thick, dark, orange oil. Heat to reflux for 16 h wash with water and brine Dry the organic layer over anhydrous sodium sulfate filter concentrate

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Dissolve (2S,4S)-4-azido-2-hydroxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester (32 g) in methanol (150 mL). Add 10% palladium on carbon (3.2 g) and hydrogenate (1 atm) at room temperature for 16 h. Filter off the catalyst through a plug of diatomaceous earth and concentrate under vacuum to obtain the title compound (28 g, crude) as a thick, yellow oil. Filter off the catalyst through a plug of diatomaceous earth concentrate under vacuum