tert-Butyl (3-aminopropyl)carbamate → (+/-)-{3-[(3-Benzyl-5-chloro-4-oxo-3,4-dihydro-pyrrolo[2,1-f][1,2,4]triazin-2-ylmethyl)-amino]-propyl}-carbamic acid tert-butyl ester

Participants

Reaction Steps

To a solution of 3-benzyl-5-chloro-4-oxo-3,4-dihydro-pyrrolo[2,1-f][1,2,4]triazine-2-carbaldehyde (Example 22 E, 50 mg, 0.17 mmol) in EtOH (1 mL) was added 4 A molecular sieves (50 mg), (3-amino-propyl)-carbamic acid tert-butyl ester (Fluka, 33 mg, 0.19 mmol) and NaBH(OAc)3 (55 mg, 0.26 mmol) under Ar. The reaction mixture was stirred at rt for 2 h, filtered and the filtrate was concentrated in vacuo. The residue was purified by flash column chromatography (SiO2, 1–2% MeOH/CHCl3) to afford the desired compound, as a colorless oil (12 mg, 16%): MS (ESI+) 446 (M++H).

Provenance & Evidence