HCID 9837097, compound → HCID 86693773, compound

Participants

Reaction Steps

A mixture of [(3R,4S)-4-azidotetrahydrofuran-3-yl]oxy-trimethyl-silane (870 mg, 4.2 mmol; prepared according to the exact procedure found in Jacobsen, E. N.; Larrow, J. F.; Schaus, S. E. J. Org. Chem. 1997, 62, 4197-4199; except that commercially available (1R,2R)-(−)-1,2-cyclohexanediamino-N,N′-bis(3,5-di-t-butylsalicylidene)cobalt (II) is used as catalyst), 10% palladium on carbon (230 mg, 216 μmol), and THF (22 mL) is stirred at room temperature under hydrogen (60 psi) for 16 h. The reaction is filtered through a pad of diatomaceous earth and the pad is rinsed with THF (50 mL). The filtrate is concentrated in vacuo to give the title compound as a brown oil (825 mg, quantitative). LC-ES/MS m/z 176 (M+1).

Provenance & Evidence