Reaction #72070

ord-9536d1429b49410b87d09dda64ceb9ae

Reaction equation

CCOC(=O)c1cc(N2CC[C@H](NC(=O)OCc3ccccc3)[C@H](OC)C2)ncc1C
ethyl cis(±)-2-(4-{[(benzyloxy)carbonyl]amino}-3-methoxypiperidin-1-yl)-5-methylpyridine-4-carboxylate
CCOC(=O)c1cc(N2CC[C@H](NC(=O)OCc3ccccc3)[C@H](OC)C2)ncc1C
Ethyl cis(±)-2-(4-{[(benzyloxy)carbonyl]amino}-3-methoxypiperidin-1-yl)-5-methylpyridine-4-carboxylate
→
CCOC(=O)c1cc(N2CC[C@H](N)[C@H](OC)C2)ncc1C
title compound
Yield 18.5%
CCOC(=O)c1cc(N2CC[C@H](N)[C@H](OC)C2)ncc1C
Ethyl cis(±)-2-(4-amino-3-methoxypiperidin-1-yl)-5-methylpyridine-4-carboxylate
Yield 18.5%

Reactants

CCOC(=O)c1cc(N2CC[C@H](NC(=O)OCc3ccccc3)[C@H](OC)C2)ncc1C
ethyl cis(±)-2-(4-{[(benzyloxy)carbonyl]amino}-3-methoxypiperidin-1-yl)-5-methylpyridine-4-carboxylate
CCOC(=O)c1cc(N2CC[C@H](NC(=O)OCc3ccccc3)[C@H](OC)C2)ncc1C
Ethyl cis(±)-2-(4-{[(benzyloxy)carbonyl]amino}-3-methoxypiperidin-1-yl)-5-methylpyridine-4-carboxylate

Reagents

[C].[Pd]
palladium-carbon

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Procedure

The same operation as in Example (160c) was performed using ethyl cis(±)-2-(4-{[(benzyloxy)carbonyl]amino}-3-methoxypiperidin-1-yl)-5-methylpyridine-4-carboxylate obtained in Example (180a) (207 mg, 0.48 mmol) and a 10% palladium-carbon catalyst (200 mg), to obtain 26.1 mg of the title compound as a yellow oily substance.

Source

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