HCID 18661335, compound → HCID 9904942, compound

Participants

Reaction Conditions

Reaction Steps

(S,S)-1-benzyl-2-oxo-3-[1'-(carboxybenzylamino)ethyl]pyrrolidine (0.51 g, 1.44 mmol) is dissolved in tetrahydrofuran (20 ml) under a N2 atmosphere. LAH (0.32 g, 8.43 mmol) is added and the reaction mixture is refluxed for 12 hours. The reaction mixture is cooled to 0° C., diluted with Et2O and quenched with 15% aqueous NaOH. The resulting mixture is filtered through a celite pad which is then washed carefully with Et2O. The filtrate is washed with 15% aqueous NaOH and the aqueous layer extracted with Et2O. The combined Et2O layers are dried over MgSO4, filtered and concentrated under a stream of N2 to give crude (R,S)-1-benzyl-3-[1'-(methylamino)ethyl]pyrrolidine: 1H NMR (300 MHz, CDCl3) δ1.04 (d, J is 6 Hz, 3H), 1.52 (m, 1H), 1.93 (m, 1H), 2.17 (m, 1H), 2.25 (dd, J is 16, 8 Hz, 1H), 2.37 (s, 3H), 2.33-2.49 (m, 2H), 2.56 (dd, J is 15, 8 Hz, 1H), 2.77 (dd, J is 8, 8 Hz, 1H), 3.58 (d, J is 12.8 Hz, 1H), 3.60 (d, J is 12.8 Hz, 1H), 7.23-7.36 (m, 5H). This crude material is suitable for use in Step 5.

Provenance & Evidence