3-Methylbutanal → 1-(3-Methylbutyl)pyrrolidine

Participants

Reaction Steps

500 mL tetrahydrofuran (THF) was placed in a 1-L suction flask. 35.3 g isovaleraldehyde (0.41 mol) and then 28.4 g pyrrolidine (0.40 mol) were mixed into the THF. 100 g of sodium triacetoxyborohydride (0.47 mol) powder was then added in 5-10 g increments to the solution. During the addition vigorous stirring was used to ensure that the powder did not clump at the bottom of the flask which would prevent the efficient mixing of the suspension. After each addition of the sodium triacetoxyborohydride powder, adequate time was provided to form a uniform slurry before the next addition of the powder. After one day the product was worked up by quenching the suspension with the slow addition of 291 g of a 27% KOH solution. The product was then extracted from the resultant solution with 500 mL pentane. The organic fraction was then collected with a separatory funnel and dried with anhydrous magnesium sulfate. The N-isopentylpyrrolidine product was then isolated by rotary evaporation of the THF and pentane solvents under reduced pressure.

Provenance & Evidence