Diisopropylethylamine → N-(tert-Butoxycarbonyl)-N-{2-[(3R)-tetrahydrofuran-3-ylamino]propyl}glycine

Participants

Reaction Steps

To a solution (0.56 M) of (3S)-tetrahydrofuran-3-amine. HCl (prepared as described in Helv. Chim. Acta 2000, 83, 1825-1845) in DCE were added N-(tert-butoxycarbonyl)-N-(2-oxopropyl)glycine (1.3 eq), DIPEA (1 eq), NaBH(OAc)3(2 eq), cat. AcOH and cat. NaOAc. Reaction mixture was irradiated at MW for 20 min at 120° C. DCE was removed under reduced pressure and the residue purified by filtration on silica gel eluting of the desired intermediate with EtOAc. Evaporation of the organic solvent yielded (II1). MS (ES) C14H26N2O5 requires: 302, found: 303 (M+H)+.

Provenance & Evidence