Benzyl Alcohol → 1-Tert-butyl 3-ethyl (3R,4S)-4-{[(benzyloxy)carbonyl]amino}pyrrolidine-1,3-dicarboxylate

Participants

Reaction Conditions

Reaction Steps

A mixture of (3S*,4S*)-1-(tert-butoxycarbonyl)-4-(ethoxycarbonyl)pyrrolidine-3-carboxylic acid (see Example 12, Step 2) (7.01 g, 24.4 mmol), benzyl alcohol (3.16 g, 29.15 mmol), diphenylphosphoryl azide (8.06 g, 29.3 mmol) and DIPEA (3.76 g, 29.15 mmol) in toluene (320 mL) was stirred at 80° C. for 15 hours. The toluene was partially evaporated, water was added and the mixture was extracted with CHCl3. The combined organic extracts were dried with Na2SO4 and evaporated. The residue was purified by column chromatography on silica gel eluting with 5→15% MeOH in CHCl3 giving the title product.

Provenance & Evidence