HCID 86755670, compound → HCID 57090370, compound

Participants

Reaction Conditions

Reaction Steps

A solution of (1S,2R,3R,5R,6S)-3-allyloxy-2-azido-bicyclo [3.1.0]hexane-2,6-dicarboxylic acid 2-benzyl ester 6-ethyl ester (XXIII-2) (28 mg, 0.073 mmol) in HOAc (0.75 mL) and H2O (0.25 mL) was hydrogenated in the presence of Pd/C (3 mg, 10% Pd/C) at 23° C. for 18 h. The catalyst was removed by filtration, the filter cake washed with 50% aqueous ethanol. After removal of the solvent in vacuum, the beige residue was refluxed in 10% HCl (1.25 mL) for 4 h. The solution was cooled to 23° C. and evaporated to dryness. The remaining pale yellow solid was dissolved in EtOH (1 mL) and propylene oxide (0.5 mL) and refluxed for 10 min, whereupon the amino acid precipiated. After cooling to 23° C., the product was filtered off, washed with ether and dried to give (1S,2R,3R,5R,6S)-2-amino-3-propoxy-bicyclo [3.1.0]hexane-2,6-dicarboxylic acid (I-8) (13 mg, 72%) as a white solid. 1H-NMR (250 MHz, D2O) □0.81 (1H, t, J=7.5 Hz), 1.48 (2H, m), 1.84 (1H, m), 2.16 (3H, m), 2.26 (1H, dd,J=12,7 Hz), 3.43 (2H, m), 3.73 (1H,bt,J=8Hz); MS[ISN] 242 [(M-H)- ]; mp >2500 C; □D20 3.72° (c=0.19, H2O).

Provenance & Evidence