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Scheme 16. Synthesis of annellated tetrahydro-P-carbolines.

Procedure

Formation of fi-carbolines 60: A solution of 3-benzyloxybenzaldehyde (1.62 g, 7.7 mmol) in toluene (10 mL) was reacted with 59 (1.7 g, 1.3 mmol) at 80° C for 18 h.The mixture was cooled to rt, filtered and washed with CH2CI2 to yield 60 (R = 3-BnO-Ph). Synthesis of lactams 62: Resin 60 (R = 3-BnO-Ph, 0.15 g, 0.11 mmol) was suspended in dry DMF (0.15 mL) and treated with NMM (49 nL, 0.45 mmol), Boc-p-alanine (64 mg, 0.34 mmol) and PyBOP (0.23 g, 0.45 mmol).The mixture was shaken at 27° C for 18 h, filtered, washed thoroughly with DMF and CH2CI2, then allowed to react with 3 % methanolic HCI (1.2 mL) at 27° C for 4 h.The resin was rinsed with CH2CI2 and then shaken with 50 % triethylamine/CH2CI2 at 27° C for 4 h.The resin was filtered and washed with CH2CI2.The combined washings were concentrated in vacuo to provide 62 (25 mg, 66 %, R = 3-BnO-Ph, n = 2) as a white solid.

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