Hydrochloric Acid → 1-(Benzo[d][1,3]dioxol-5-ylmethyl)pyrrolin-3-ol

Participants

Reaction Steps

A solution of pyrrolidin-3-ol (0.539 g, 6.2 mmol) in ethyleneglycol dimethylether (DME) (5 mL) was treated with benzo[d][1,3]dioxole-5-carbaldehyde (272) (1.08 g, 7.2 mmol) and dibutyldichlorostannane (0.71 g, 2.3 mmol). After the suspension was stirred for 15 min at room temperature, phenylsilane (1.0 mL, 8.6 mmol) was added neat and the mixture was stirred for 18 h. The reaction mixture was diluted with DCM (50 mL), treated with 1N HCl (13 mL) and stirred for 30 min followed by dilution with H2O (50 mL) and DCM (50 mL). The aqueous layer was collected, basified with solid potassium carbonate (K2CO3), extracted with DCM, dried over MgSO4, filtered and concentrated to provide title compound 273 (0.82 g, 60% yield).

Provenance & Evidence