(S)-1,7-diazaspiro[4.4]nonane synthesis

Yield:1311534-72-1 84%

Reaction Conditions:

with hydrogen;Pd(OH)2/C in methanol; under 2585.81 Torr;

Steps:

16

The above 1-benzyl-7-((R)-α-methylbenzyl)-1 ,7-diazaspiro[4.4]nonane (0.90 g, 2.8 mmol) was dissolved in methanol (50 mL), and combined with 20% palladium hydroxide on carbon (wet, Degussa type) (0.2 g). The mixture was shaken under hydrogen atmosphere (50 psi) for 3 d, with an additional 0.2 g of catalyst added on day 2. The mixture was filtered through Celite, and the filtrate was concentrated. The residual oil was subjected to Kugelrohr (bulb-to-bulb) distillation (80⁰C, ~1 mm Hg pressure) to give a colorless oil (1 ,7- diazaspiro[4.4Jionane, 300 mg, 84%). This was used directly in the next step without further characterization.

References:

WO2009/91561,2009,A1 Location in patent:Page/Page column 43