Morpholine → HCID 69707996, compound

Participants

Reaction Steps

To a solution of (S)-2-t-butoxycarbonylamino-3-(3-allyloxycarbonylbenzyloxy)-propionitrile (8.0 g, 22.22 mmol) in THF (100 mL) is added morpholine (19.4 mL, 222 mmol). After deoxygenation with bubbling nitrogen (2 min.), Pd(PPh3)4 (1.28 g, 1.11 mmol) is added in one portion, and the solution is stirred 1 h. Solvent is evaporated, the residue is taken up in EtOAc (250 mL), and washed with 1 N HCl (250 mL), brine (100 mL), dried (MgSO4), evaporated, and the residue chromatographed (silica, 2% methanol, CH2Cl2) to yield (S)-2-t-butoxycarbonylamino-3-(3-carboxybenzyloxy)-propionitrile, as a light yellow oil.

Provenance & Evidence