Sodium Azide → tert-Butyl 2-azido-7-azaspiro[3.5]nonane-7-carboxylate

HRID 336521Notes

Reaction equation

HRID 336521 reaction equation
CS(O[CH:6]1[CH2:9][C:8]2([CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH2:10]2)[CH2:7]1)(=O)=O.[N-:22]=[N+:23]=[N-:24].[Na+]>CN(C)C=O>[N:22]([CH:6]1[CH2:9][C:8]2([CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH2:10]2)[CH2:7]1)=[N+:23]=[N-:24]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 22248489tert-Butyl 2-((methylsulfonyl)oxy)-7-azaspiro[3.5]nonane-7-carboxylate

Product 1

HCID 86660638tert-Butyl 2-azido-7-azaspiro[3.5]nonane-7-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 5.90 g (18.47 mmol) of tert-butyl 2-methanesulfonyloxy-7-azaspiro[3.5]nonane-7-carboxylate (WO 2003/084 948) and 3.60 g (55.41 mmol) of sodium azide in 27 mL of N,N-dimethylformamide is refluxed for 12 hours under an inert atmosphere.

Sources & evidence

ORD record
ord-19adc2477eeb4cbdabe7ce8a4da3e8b9
Source dataset
uspto-grants-2014_11
Patent number
US08889702B2

Reaction notes

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