Triphenylphosphine → 1-Cyclopentylamino-1-(thioacetylmethyl)cyclopentane

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Reaction Steps

To a 0° C. solution of Ph3P (27.9 g, 0.107 mol, 1.3 equiv.) in anh. THF (400 mL) were successively added diisopropyl azodicarboxylate (21.5 g, 0.107 mol, 1.3 equiv.) and 1-cyclopentylamino-1-(hydroxymethyl)cyclopentane (Method B4d; 15.0 g, 0.082 mol). The resulting slurry was stirred for 30 min., then was treated with thiolacetic acid (7.6 mL, 0.107 mol, 1.3 equiv.). The resulting yellow solution was stirred for 15 min. and concentrated under reduced pressure to about 100 mL. The residue was dissolved in EtOAc (200 mL) and the resulting solution was extracted with a 1N HCl solution (5×125 mL). The combined aqueous layers were washed with EtOAc (2×200 mL), neutralized with K2CO3 to pH 7.0-7.5, then extracted with EtOAc (5×200 mL). The organic layers were combined, dried (Na2SO4) and concentrated under reduced pressure. The residue was dried in vacuo to afford 1-cyclopentylamino-1-(thioacetylmethyl)cyclopentane as a yellow oil (19.1 g): TLC (10% EtOAc/hexanes) Rf0.16; 1H NMR (CDCl3) δ1.20-1.87 (m, 16H), 2.34 (s, 3H), 2.92-3.02 (m, 1H), 3.15 (s, 2H); 13C NMR (CDCl3) δ23.9, 25.2, 29.3, 36.4, 40.1, 55.8, 73.0, 169.8; CI-LRMS m/z (rel abundance) 242 ((M+H)+, 100%).

Provenance & Evidence