Sodium Azide → HCID 59438450, compound

Participants

Reaction Conditions

Reaction Steps

g (3.212 mmol) 3-Hydroxy-3-phenyl-piperidine-1-carboxylic acid benzyl ester was dissolved in a cold mixture (10° C.) of trifluoroacetic acid (12.3 ml) and water (2.0 ml). The solution was cooled to 0° C. and 1.46 g (22.48 mmol) sodium azide were added portionwise. The temperature rose to 10° C. The ice bath was removed and the mixture was stirred at room temperature for 3 hours. The mixture was cooled in an ice bath and basified by dropwise addition of a 25% ammonium hydroxide solution (13.0 ml) maintaining the temperature below 20° C. The mixture was diluted with water (45 ml) and extracted 3 times with dichloromethane. The combined extracts were washed once with brine, dried over sodium sulfate, filtered and concentrated in vacuo to provide the title compound as a light yellow oil which was used in the next step without further purification.

Provenance & Evidence