1-((tert-butoxy)carbonyl)-3-(((9H-fluoren-9-ylmethoxy)carbonyl)amino)piperidine-3-carboxylic acid → 3-Amino-1-(tert-butoxycarbonyl)piperidine-3-carboxylic acid

Participants

Reaction Steps

1-(tert-butoxycarbonyl)-3-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}piperidine-3-carboxylic acid was resolved by chiral HPLC resolution {Merck 50 mm 16 μm Kromasil Chirose 2 No. CT9014, tert-butylmethylether/iso-propanol (90/10). The second eluted enantiomer (800 mg, 1.71 mmol) 1-(tert-butoxycarbonyl)-3-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}piperidine-3-carboxylic acid (Isomer 2) was deprotected using an analogous procedure to that described for the equivalent step in Example 89 to give 3-amino-1-(tert-butoxycarbonyl)piperidine-3-carboxylic acid (Isomer 2); 1H NMR Spectrum: (D2O) 1.44 (s, 9H); 1.63 (m, 1H); 1.79 (d, 1H); 1.97 (d, 1H); 2.10 (m, 1H); 2.88 (t, 1H); 3.33 (d, 1H); 4.09 (m, 2H).

Provenance & Evidence