Triethylamine → tert-Butyl (S)-(1-(dimethylamino)-1-oxo-3-phenylpropan-2-yl)carbamate

Participants

Reaction Steps

A solution of dimethylamine hydrochloride (1.45 g, 17.8 mmol) in DMF (46 mL) was cooled to −10° C. and triethylamine (2.7 mL, 19.4 mmol) was added. N-Boc-L-phenylalanine (4.59 g, 17.3 mmol, Aldrich) and HOBt (3.49 g, 26 mmol) were then added and the reaction stirred for 5 min before addition of EDCI (3.33 g, 17.4 mmol). The reaction mixture was left to stir for 16 h then diluted with ethyl acetate (400 mL), washed sequentially with aqueous sodium hydroxide solution (2M, 2×100 mL), hydrochloric acid (2N, 2×100 mL), brine (250 mL) and then dried (MgSO4). Evaporation in vacuo gave the title compound as a pale yellow oil. δH (CDCl3): 1.41 (9H, s), 2.61, 2.85 (6H, 2s), 2.91–2.99 (2H, m), 4.83 (1H, m), 5.40 (1H, br d), 7.18–7.29 (5H, m).

Provenance & Evidence