Hydrochloric Acid → Methyl 4-{methyl[4-(pyrrolidin-1-yl)but-2-yn-1-yl]amino}-4-oxobutanoate

Participants

Reaction Steps

Dowex 50 resin (200 mg) which had been activated with HCl was added to a solution of N-Methyl-N-[4-(1-pyrrolidinyl)-2-butynyl]-3-carboxypropanamide (101 mg, 0.40 mmol) in MeOH (2 mL) and the suspension was vigorously stirred overnight. The resin was filtered off and washed thoroughly with TFA. The combined MeOH and TFA washes were evaporated under a stream of N2, neutralized with 2M Na2CO3 solution and the product was extracted into EtOAc (3× mL). The organic layer was dried over Na2CO3, evaporated in vacuo and purified on silica gel (CHCl3 /MeOH/NH4OH, 40/10/1) to give 009 (66.8 mg, 63% yield). MS (CI-NH3), m/e 267 (MH+), 186, 172. 1H NMR (CDCl3) δ1.79 (br s, 4 H), 2.58 (br s, 4 H), 2.64 (m, 4 H), 2.98 & 3.07* (s, 3 H), 3.38 (s, 2 H), 3.68 (s, 3 H), 4.08 & 4.24* (s, 2 H).

Provenance & Evidence