1-Pyrrolidineethanamine → Ammonia

Participants

Reaction Steps

1-(2-Aminoethyl)pyrrolidine (83 μL, 0.63 mmol) was added to a mixture of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (122 mg, 0.63 mmol), 3-{2-[(2R)-2-(tert-butyldimethylsilanyloxy)-2-(4-hydroxy-3-hydroxy methyl-phenyl)ethylamino]-2-methylpropyl}benzoic acid (preparation 37) (200 mg, 0.42 mmol), 1-hydroxybenzotriazole hydrate (63 mg, 0.47 mmol) and N,N-diisopropylethylamine (88 □L, 0.63 mmol) in N,N-dimethylformamide (5 mL). The resulting solution was stirred for 18 hours at room temperature. The solvent was removed in vacuo and the residue was partitioned between ethyl acetate (50 mL) and saturated sodium hydrogen carbonate solution (10 mL). The aqueous layer was separated and re-extracted with dichloromethane (30 mL), and the combined organic solution was dried (sodium sulfate) and concentrated in vacuo to give a yellow oil. The oil was purified by flash column chromatography on silica gel eluting with dichloromethane:methanol:0.88 ammonia, 100:0:0 to 75:25:2 to afford the title compound as a pale yellow solid. 1H NMR (400 MHz, CD3OD) δ: 7.69 (2H, m) 7.40-7.31 (2H, m), 7.26 (1H, m), 7.14-7.03 (1H, dd), 6.85 (1H, d), 4.69 (1H, m), 4.62 (2H, m), 3.58 (2H, m), 2.89-2.59 (10H, m), 1.82-1.79 (4H, m), 1.12 (3H, s), 1.07 (3H, s), 0.79 (9H, s), −0.01 (3H, s), −0.21 (3H, s) ppm; LRMS APCI m/z 570 [M+H]+

Provenance & Evidence