Hydrochloric Acid → HCID 68019346, compound

Participants

Reaction Steps

To a solution of tert-butyl (3R,4R)-4-azido-1-benzylpyrrolidin-3-ylcarbamate (7.0 g, 22.0 mmol) in 250 mL toluene, PPh3 6.0 g, 23.0 mmol) was added and the mixture was refluxed for 1 hour. The mixture was cooled down to room temperature, diluted with 250 mL THF, water (0.54 g, 30.0 mmol) was added and the mixture was refluxed for an additional 1 hour. 4N HCl was added, the aqueous acidic layer was separated, washed with CHCl3 and basified with aqueous NH3 to pH 9-10. The product 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 10% MeOH in CHCl3 giving the title mono-Boc protected diamine.

Provenance & Evidence