Water → HCID 69413841, compound

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Reaction Steps

(3aRS,4RS,6aSR)-4-[(3S)-3-(4-fluorobenzyl)piperidin-1-yl]-2-trityloctahydrocyclo-penta[c]pyrrole (500 mg, 918 μmol) was dissolved in trifluoroacetic acid (4 mL) to form a dark orange-yellow solution. Water (5 mL) was added dropwise to form a dense slurry, lighter in color. After 40 minutes, the mixture was concentrated under vacuum. The residue was dissolved in ethyl acetate and extracted with 1.0 N aqueous hydrochloric acid. The aqueous phase was washed with ethyl acetate, and then made strongly basic by the addition of 50% aqueous sodium hydroxide. The resulting mixture was extracted several times with ether, and the combined ether phases were dried over sodium sulfate and concentrated, yielding a gum (263 mg, 95%), which was used without further purification. 1H NMR (300 MHz, CDCl3) δ 7.08 (m, 2H), 6.95 (m, 2H), 3.14 (m, 1H), 3.0-2.6 (m, 4H), 2.6-2.3 (m, 7H), 2.0-1.2 (m, 9H), 0.93 (m, 1H). Mass spec (CH4-CI) m/z 303.2 (M+H+, 100%).

Provenance & Evidence