(3R,6R)-methyl 6-methylpiperidine-3-carboxylate synthesis

Yield: 100%

Reaction Conditions:

with potassium carbonate in dichloromethane;water at 20; for 1 h;

Steps:

Preparation of (3R,6R)-Methyl 6-Methylpiperidine-3-carboxylate (6-313α1-Me) A solution of 2 M aqueous potassium carbonate (14 mL) was added to 6-314α1-Me/L-DBTA salt (9.78 g) in CH₂Cl₂ (14 mL). The reaction mixture was allowed to stir at room temperature for 1 hour before the phases were separated. The aqueous phase was extracted with CH₂Cl₂ (2*50 mL) and the combined organic phases were dried (Na₂SO₄), filtered, and concentrated under reduced pressure to afford 6-313α1-Me (4.47 g, 100% of theory, 98% ee by HPLC after Mosher's acid chloride derivatization, HPLC Method A).

References:

Prexa Pharmaceuticals, Inc. US2010/93706, 2010, A1 Location in patent:Page/Page column 47-48