Phthalimide → HCID 69332180, compound

Participants

Reaction Steps

To a stirred solution of cis-1tert-butoxycarbonyl-(2S)-(tert-butyldiphenylsilyloxy)methyl-4-hydroxypyrrolidine (1.82 mg, 4.0 mmol), phthalimide (647 mg, 4.4 mmol), and Ph3P (1.26 g, 4.8 mmol) in THF (20 ml) was added DIAD (889 mg, 4.4 mmol) at 0° C. The reaction mixture was stirred at room temperature for 18 hr. The mixture was concentrated in vacuo. The residue was purified by column chromatography on silica gel with n-hexane-EtOAc (5/1, v/v) as eluent to give N-[cis-1tert-butoxycarbonyl-(2S)-(tert-butyldiphenylsilyloxy)methyl-4-pyrrolidinyl]phthalimide (1.6 g, 69%) as an amorphous solid. 1H-NMR (CDCl3) δ 1.07 (s, 9H), 1.30 and 1.44 (each s, total 9H), 2.27–2.37 (m, 1H), 2.94–2.96 (m, 1H), 3.81–4.09 (m, 51H), 4.72 (m, 1H), 7.37–7.38 (m, 6H), 7.67–7.74 (m, 6H), 7.84–7.86 (m, 2H).

Provenance & Evidence