Reaktion #72033

ord-f7084e78cd4e493192a1becde05d7c28

Reaktionsgleichung

O=C([O-])[O-].[Cs+].[Cs+]
cesium carbonate
CO[C@@H]1CNCC[C@@H]1NC(=O)OCc1ccccc1.Cl
benzyl cis(±)-[3-methoxypiperidin-4-yl]carbamate hydrochloride
CCOC(=O)c1cncc(Br)c1
ethyl 5-bromopyridine-3-carboxylate
c1ccc(P(c2ccccc2)c2ccc3ccccc3c2-c2c(P(c3ccccc3)c3ccccc3)ccc3ccccc23)cc1
BINAP
CCOC(=O)c1cncc(N2CC[C@H](NC(=O)OCc3ccccc3)[C@H](OC)C2)c1
title compound
Ausbeute 51.2%
CCOC(=O)c1cncc(N2CC[C@H](NC(=O)OCc3ccccc3)[C@H](OC)C2)c1
Ethyl cis(±)-5-(4-{[(benzyloxy)carbonyl]amino}-3-methoxypiperidin-1-yl)pyridine-3-carboxylate
Ausbeute 51.2%

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Vorschrift

The same operation as in Example (160b) was performed using benzyl cis(±)-[3-methoxypiperidin-4-yl]carbamate hydrochloride obtained in Example (160a) (832 mg, 2.76 mmol), ethyl 5-bromopyridine-3-carboxylate (530 mg, 2.3 mmol), palladium acetate (51.72 mg, 0.23 mmol), BINAP (286.89 mg, 0.46 mmol), and cesium carbonate (2.25 g, 6.91 mmol), to obtain 487 mg of the title compound as a yellow oily substance.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08536197B2uspto-grants-2013_09