Chlorotrimethylsilane → 4-(8-Phenyl-1,4-dioxaspiro[4.5]dec-8-yl)pyrrolidine hydrochloride

Participants

Reaction Steps

The aminonitrile 8-pyrrolidin-1-yl-1,4-dioxaspiro[4,5]decane-8-carbonitrile (10.0 g, 42.6 mmol), dissolved in THF (90 ml), was added under argon and with ice cooling within 15 min to a 1.82M phenyl magnesium chloride solution in THF (70 ml, 0.127 mol) and the mixture was stirred for 16 h at room temperature. The reaction mixture was processed by adding saturated ammonium chloride solution (100 ml) with ice cooling and was then extracted with diethyl ether (3×100 ml). The organic phase was extracted by shaking with water (70 ml) and saturated NaCl solution (70 ml) and concentrated to small volume. A yellow crystal paste (11.8 g) was retained which in addition to the desired product still contained the ketal 8-pyrrolidin-1-yl-1,4-dioxaspiro[4,5]decane-8-carbonitrile. The crude product was dissolved in ethyl methyl ketone (70 ml) and ClSiMe3 (8 ml, 0.063 mol) was added with ice cooling. After a reaction time of 6 h the hydrochloride 4-(8-phenyl-1,4-dioxaspiro[4,5]dec-8-yl)pyrrolidine hydrochloride was able to be isolated as a white solid in a yield of 43% (5.9 g).

Provenance & Evidence