Hydrogen Cyanide → 3-Methyl-1-phenyl-1,3,7-triaza-spiro[4.5]decan-4-one

A solution comprising of 3-Oxo-piperidine-1-carboxylic acid tert-butyl ester (2.5 g, 12.55 mol) and aniline (1.28 g, 13.8 mmol) in acetic acid (10 ml) was stirred at RT for 60 mins under nitrogen. Trimethylsilyl cyanide (1.57 ml, 12.55 mmol) was added carefully into the reaction mixture. The reaction mixture was left to stir at RT for a further 90 mins. The reaction mixture was cannulated into a rapidly stirring flask containing crushed ice (50 ml) and concentrated ammonium hydroxide (30 ml) for 10 minutes, resulting in a precipitate. This solution was allowed to stir for a further 15 mins to ensure no HCN remained before adding EtOAc (150 ml) to dissolve the precipitate. The organics were then separated and the aqueous washed with a further EtOAc (50 ml). The organics portions were combined, washed with brine (100 ml), dried (MgSO4) and concentrated in vacuo to afford an oil. Purification of the crude product by chromatography on silica eluting with 0-50% EtOAc in iso-hexane afforded the title compound.

1. waitThe reaction mixture was left
2. stirringa rapidly stirring flask
3. additioncontaining
4. customresulting in a precipitate
5. stirringto stir for a further 15 mins
6. dissolutionto dissolve the precipitate
7. customThe organics were then separated
8. washthe aqueous washed with a further EtOAc (50 ml)
9. washwashed with brine (100 ml)
10. dry with materialdried (MgSO4)
11. concentrationconcentrated in vacuo
12. customto afford an oil
13. customPurification of the crude product by chromatography on silica eluting with 0-50% EtOAc in iso-hexane

ORDレコード

ord-8d0c34f92c464e5ebd97d6499c077d0f

出典データセット

uspto-grants-2013_10

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08546416B2