Trifluoroacetic acid → HCID 54343518, compound

Participants

Reaction Steps

To a round-bottomed flask was added crude benzyl 1-(6-chloropyridin-3-yl)-3,4-dihydroisoquinoline-2(1H)-carboxylate (170 mg, 449 μmol), CH2Cl2 (10 mL) and TFA (10 mL). The reaction was allowed to stir at RT. After 3 days, LC-MS shows little progress. The reaction was concentrated in vacuo to remove CH2Cl2 and the resulting solution allowed to stir for another 3 days, then cautiously poured into 10% Na2CO3 and extracted with CH2Cl2 (3×20 mL). The combined organic layers were concentrated in vacuo and purified by reverse-phase preparative HPLC (Shimadzu) on a Phenomenex Gemini® column (5 micron, C18, 110 Å, Axia, 100×50 mm) eluting at 90 mL/min with an linear gradient of 10% to 100% MeCN (0.1% TFA) in water (0.1% TFA) over 20 min to give crude 1-(6-chloropyridin-3-yl)-1,2,3,4-tetrahydroisoquinoline as a white solid. The crude solid was carried into the next step. MS (ESI pos. ion) m/z: 245 (M+1).

Provenance & Evidence