Chloroform → Tert-butyl 2-(4-aminophenyl)pyrrolidine-1-carboxylate

Participants

Reaction Steps

LiHMDS (1.6 g, 9.6 mmol) is added to a 100 mL round bottom flask. Toluene (20 mL) is added followed by addition of Pd2(dba)3.CHCl3 (50 mg, 0.05 mmol) and P(tBu)3.HBF4 (40 mg, 0.14 mmol). 2-(4-Bromo-phenyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (1.5 g, 4.6 mmol) is added to the flask. After degasing, the mixture is stirred at room temperature overnight. After TLC suggested no starting bromide is left, the reaction mixture is diluted with ether and poured into dilute HCl (aq). The ether layer is discarded, the aqueous layer is basified with NH4OH and extracted with EtOAc. The EtOAc layer is dried and concentrated to provide the desired product (1.0 g, 83%). 1H NMR (300 MHz, CDCl3) ∂ 6.94-6.96 (2H, m), 6.60-6.67 (2H, m), 4.67-4.85 (1H, m), 3.58 (4H, br), 2.24 (1H, m), 1.73-1.97 (3H, m), 1.44 (3H, s), 1.21 (6H, s).

Provenance & Evidence