tert-butyl (3R)-3-aminopiperidine-1-carboxylate → (3R)-tert-Butyl 3-(1-(4-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydroisoquinoline-2-carboxamido)piperidine-1-carboxylate

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Reaction Steps

A mixture of 4-nitrophenyl 1-(4-(trifluoromethyl)phenyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate (350 mg, 0.79 mmol, example 15) and (R)-1-Boc-3-amino-piperidine (1.6 mL, 7.91 mmol) was subjected to a microwave irradiation at 120° C. for 45 min. Then, MeOH (2 mL) was added to the mixture and the mixture was filtered. The solution mixture was purified by preparative HPLC (10%-100% of MeCN (0.1% TFA)/H2O (0.1% TFA). All fractions of the product were combined, saturated NaHCO3 (1 mL) was added and the solvents were removed. Then, an additional amount of saturated NaHCO3 (10 mL) was added and the aqueous mixture was extracted with EtOAc (2×10 mL). The combined organic extracts were dried over MgSO4 and concentrated to give the title compound as a white solid. MS (ESI, positive ion) m/z: 504 (M+H).

Provenance & Evidence