Sodium Azide → tert-Butyl 2-azido-6-azaspiro[3.4]octane-6-carboxylate

HRID 336526Notes

Reaction equation

HRID 336526 reaction equation
CS(O[CH:6]1[CH2:9][C:8]2([CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10]2)[CH2:7]1)(=O)=O.[N-:21]=[N+:22]=[N-:23].[Na+]>CN(C)C=O.C(OCC)(=O)C.O>[N:21]([CH:6]1[CH2:9][C:8]2([CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10]2)[CH2:7]1)=[N+:22]=[N-:23]

Participants

6

Reactant 2

HCID 33557Sodium AzideHCID 86660639tert-Butyl 2-[(methylsulfonyl)oxy]-6-azaspiro[3.4]octane-6-carboxylate

Product 1

HCID 86660640tert-Butyl 2-azido-6-azaspiro[3.4]octane-6-carboxylateYield 99.7%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 0.46 g (1.51 mmol) of tert-butyl 2-methanesulfonyloxy-6-azaspiro[3.4]octane-6-carboxylate, prepared in step 6.2., and 0.19 g (3.01 mmol) of sodium azide in 5 mL of N,N-dimethylformamide is refluxed for 12 hours under an inert atmosphere. The reaction medium is allowed to cool to room temperature and is then taken up in ethyl acetate and water. The aqueous phase is separated out and extracted twice with ethyl acetate, and the combined organic phases are washed with saturated aqueous ammonium chloride solution and dried over sodium sulfate. After evaporating off the solvent, 0.380 g of product is obtained in the form of an orange-coloured oil, which is used without further purification in the following step.

Workup

  1. customThe aqueous phase is separated out
  2. extractionextracted twice with ethyl acetate
  3. washthe combined organic phases are washed with saturated aqueous ammonium chloride solution
  4. dry with materialdried over sodium sulfate
  5. customAfter evaporating off the solvent

Sources & evidence

ORD record
ord-5b956eaf1da5471abd6a598dd254e447
Source dataset
uspto-grants-2014_11
Patent number
US08889702B2

Reaction notes

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