Water → HCID 68567319, compound

Participants

Reaction Steps

4.3 mL (14.3 mmol) of titanium isopropoxide and 1.9 g (5 mmol) of (S)-2-(tert-butoxycarbonylamino)-propionaldehyde (prepared according to the method described by Itaya, Taisuke et al., Tetrahedron Lett., 1986, 52(27), 6349-52) are added to a solution of 1.88 g (33 mmol) of cyclopropylamine in 10 mL of anhydrous methanol. The solution is stirred for 5 hours at room temperature then 227 mg (6 mmol) of sodium borohydride is added. Stirring is continued for a further 2 hours then 2 mL of water is added. The reaction mixture is filtered then the solvents are evaporated. The residue is purified by chromatography on silica (eluent dichloromethane/methanol 98/2) to give 400 mg (17%) of (S)—N′-tert-butoxycarbonyl-N-cyclopropyl-propane-1,2-diamine in the form of a colourless oil.

Provenance & Evidence