Triethylamine → (S)-1-Benzyl-3-mesyloxypyrrolidine

Participants

Reaction Steps

(S)-1-Benzyl-3-hydroxypyrrolidine (1003.5 g, 5.66 mol) was dissolved in toluene (12 L) and the solution stirred and cooled to 0°-5° C. Triethylamine (680 g, 6.67 mol) was added followed by methanesulfonyl chloride (760 g, 6.63 mol) over a 4 hour period. A slurry formed after 30 minutes. The mixture was allowed to stir an additional 1.5 hours and 7% sodium bicarbonate (12 L) was added to the reaction mixture and the organic layer separated. The aqueous layer was extracted with toluene (4 L and 2 L) and the combined organic layers washed with saturated sodium bicarbonate (3×6 n) , dried over MgSO4 and concentrated under reduced pressure to give (S)-1-benzyl-3-mesyloxy-pyrrolidine as a yellow oil (1.41 kg, 98%): 1HNMR (CDCl3, 200 MHz): δ2.0-2.6 (m, 4H), 2.85 (d, 2H, J=5), 2.97 (δ , 3H), 3.65 (AB, 2H, J=3), 5.20 (m, 1H), 7.3 (m, 5H).

Provenance & Evidence