octahydro-1H-pyrrolo[3,4-b]pyridine

Octahydro-1H-pyrrolo[3,4-b]pyridine is a chemical compound with the molecular formula C7H14N2 and a molecular weight of 126.2 . It is also known by its IUPAC name (4aR,7aR)-octahydro-1H-pyrrolo[3,4-b]pyridine . It is used as an intermediate in the synthesis of moxifloxacin, a fluorinated quinolone antibacterial .

Synthesis Analysis

A novel synthesis of (4aS,7aS)-octahydro-1H-pyrrolo[3,4-b]pyridine has been demonstrated, which involves the recovery and reuse of chiral auxiliary naproxen . The synthesis involves stereoselective reduction procedures on 6-benzyl-5H-pyrrolo[3,4-b]pyridine-5,7(6H)-dione, enabling the desired chirality in the nonane .

Molecular Structure Analysis

The molecular structure of octahydro-1H-pyrrolo[3,4-b]pyridine consists of a pyrrolo and a pyridine ring . The structure can present two isomeric structures: 1H-pyrrolo[3,4-b]pyridines and 2H-pyrrolo[3,4-b]pyridines .

Chemical Reactions Analysis

The synthesis of octahydro-1H-pyrrolo[3,4-b]pyridine involves chemical reactions that enable the desired chirality in the nonane . This process involves the recovery and reuse of chiral auxiliary naproxen .

Physical And Chemical Properties Analysis

Octahydro-1H-pyrrolo[3,4-b]pyridine is a colorless to orange solid or liquid . It has a density of 1.0±0.1 g/cm3, a boiling point of 198.5±8.0 °C at 760 mmHg, and a vapor pressure of 0.4±0.4 mmHg at 25°C . The compound has a molar refractivity of 37.0±0.3 cm3, and its surface tension is 31.6±3.0 dyne/cm .