Reaktion #697
ord-3016ae12f45142f49e43a15eaa293eb1
Reaktionsgleichung
Lösungsmittel
Reaktionsbedingungen
Vorschrift
Vial 1) Pd2(dba)3 (0.018 g, 0.02 mmol) and BINAP (0.024 g, 0.04 mmol) were mixed in toluene (1mL) under N2 and stirred at rt for 5min. Vial 2) sodium tert-butoxide (0.999 g, 10.08 mmol), tert-butyl (R)-3-aminopiperidine-1-carboxylate (1.249 g, 6.05 mmol) and 2-chloropyridine (0.477 mL, 5.04 mmol) were mixed in toluene (6mL) under N2. Added the catalyst solution from vial 1. The mixture was heated at 110°C in an oil-bath. LCMS (3h): product, no SM left. The reaction was cooled to rt and the solvent was evaporated. Added EtOAc, washed with water. Purified by column chromatography (using SP4 TM HPFC system, KP-Sil (50g) column, A=heptane, B=EtOAc/2M NH3 in MeOH (9/1), 27mL/fr, (0% B 2CV, 0-30% B 10CV, 30% B 2CV)) to yield tert-butyl (R)-3-(pyridin-2-ylamino)piperidine-1-carboxylate (1.306 g, 93 %) as yellow solid. [M+H]+ 278. 1H NMR (400 MHz, CDCl3) d 1.42 (s, 9H), 1.51 - 1.64 (m, 2H), 1.68 - 1.8 (m, 1H), 1.93 - 2.05 (m, 1H), 2.81 - 3.36 (m, 2H), 3.45 - 4.16 (m, 3H), 4.50 (d, 1H), 6.42 (d, 1H), 6.5 - 6.62 (m, 1H), 7.36 - 7.45 (m, 1H), 8.02 - 8.13 (m, 1H). Expected Number of Hs: 23 Assigned Hs: 23.