Toluene → (3S)-(-)-3-(tert-Butoxycarbonylamino)pyrrolidine

Participants

Reaction Steps

To a solution of 2-(trimethylsilyl)ethanol (33 mL) in toluene (80 mL) is added 4-dimethylaminopyridine (0.82 g), under N2. Compound 1 (11.4 g) (prepared in the same manner as Compound 3 in Example 24) is added and the mixture is heated to reflux. Upon completion, the reaction mixture is cooled and saturated ammonium chloride (125 mL) is added, followed by the addition of EtOAc (150 mL). The layers are separated and the EtOAc portion is washed with water (4×50 mL) and brine (2×40 mL), and dried (MgSO4). The solvents are removed in vacuo and the residue is subjected to column chromatography (silica) to provide Compound 2.

Provenance & Evidence