Nitrogen → HCID 10837709, compound

Participants

Reaction Steps

The product was prepared as described in J.O.C., 1998, 63 (23), 8432-8439, starting from a solution of N,N′-bis(benzyloxycarbonyl)guanidine (prepared as described in J.O.C., 1998, 63 (23), 8432-8439), (3 g, 9.17 mmol) in anhydrous THF which was brought to T=−45° C., after which NaH (60% in mineral oil, 728 mg, 18.1 mmol) was added piecemeal in small portions. The suspension was kept at T=−45° C. for 1 hour after which benzylchloroformiate (1.55 g, 9.17 mmol) was added and the suspension was brought back to room temperature in an N2 atmosphere and left under stirring for 18 hours. The mixture was concentrated at reduced pressure, and then diluted with CH2Cl2 and H2O; the two phases were separated, the organic phase was washed with HCl 1N, NaCl s.s. and dried on anhydrous Na2SO4. The crude reaction product was purified by silica gel chromatography using CH2Cl2/Et2O as eluent to give 810 mg of product (yield: 19%). Analytical data as reported in the literature.

Provenance & Evidence