Tetrabutylammonium Fluoride → trans-1-tert-butoxycarbonyl-4-dimethylamino-(2S)-hydroxymethylpyrrolidine

Participants

Reaction Steps

To a stirred solution of trans-1tert-butoxycarbonyl-(2S)-(tert-butyldiphenylsilyloxy)methyl-4-dimethylaminopyrrolidine (330 mg, 0.68 mmol) in THF (5 ml) was added TBAF (1.0 M solution in THF, 1.0 ml, 1.0 mmol) at 0° C. The reaction mixture was stirred at room temperature for 2 hr. The mixture was concentrated in vacuo. The residue was purified by column chromatography on silica gel with MeOH—CH2Cl2 (3:97 to 20:80, v/v) as eluent to give trans-1-tert-butoxycarbonyl-4-dimethylamino-(2S)-hydroxymethylpyrrolidine (180 mg, quant.) as a pale yellow oil. 1H-NMR (CDCl3) δ 1.47 (s, 9H), 2.23 (s, 6H), 1.65–1.75 (m, 2H), 2.75–4.10 (m, 4H), 3.61 (d, J=5.6 Hz, 2H).

Provenance & Evidence