Dicyclohexylcarbodiimide → 3-(3-Pyridyl)-1-propyl N-(tert-butyloxycarbonyl)pyrrolidine-2-carboxylate

Beteiligte Stoffe

Reaktionsschritte

A mixture of N-(tert-butyloxycarbonyl)-(S)-proline (6.0 g; 28 mmol), 3-(3-pyridyl)-1-propanol (5.80 g; 41.8 mmol), dicyclohexylcarbodiimide (9.20 g; 44.48 mmol), camphorsulfonic acid (21.60 g; 9.26 mmol), and 4-dimethylaminopyridine (1.12 g; 9.26 mmol) in dry methylene chloride (200 mL) was stirred overnight. The reaction mixture was filtered through Celite, concentrated, and purified on a silica gel column eluting with 40% ethyl acetate in hexane to obtain 5.0 g of the product as a clear oil (53%). 1H NMR (300 MHz, CDCl3): δ1.42 (s, 9H); 1.43-1.95 (m, 6H); 2.68 (m, 2H); 3.46-3.52 (m, 2H); 4.11-4.22 (m, 2H); 4.33 (m, 1H); 7.17-7.24 (m, 1H); 7.47 (m, 1H); 8.43 (s, 2H).

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