4-Fluorophenol → HCID 44600363, compound

Participants

Reaction Steps

To a solution of (2S,4R)-2-(4-cyclobutyl-[1,4]diazepane-1-carbonyl)-4-hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester (1.74 g, 4.73 mmol) in THF (24 mL) was added 4-fluorophenol (795 mg, 7.10 mmol), triphenylphosphine (1.86 g, 7.10 mmol), and DEAD (1.12 mL, 7.10 mmol). After 48 h, the mixture was diluted with 1 M NaOH and extracted with CH2Cl2 (3×). The combined organic layers were dried and concentrated. Purification by FCC provided the desired product (969 mg, 44%). MS (ESI): mass calcd. for C25H36FN3O4, 461.27; m/z found, 462.6 [M+H]+. 1H NMR (CDCl3): 6.98-6.89 (m, 2H), 6.79 (dd, J=8.5, 4.1 Hz, 2H), 4.81-4.74 (m, 1H), 4.71-4.51 (m, 1H), 4.03-3.90 (m, 1H), 3.79-3.59 (m, 2H), 3.59-3.41 (m, 3H), 2.88-2.73 (m, 1H), 2.68-2.29 (m, 5H), 2.18-2.06 (m, 1H), 2.04-1.94 (m, 2H), 1.93-1.70 (m, 4H), 1.69-1.53 (m, 2H), 1.46-1.40 (m, 9H).

Provenance & Evidence