Water → Tert-butyl 3-azidoazetidine-1-carboxylate

HRID 1371773Notes

Reaction equation

HRID 1371773 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:11][CH:10](OS(C)(=O)=O)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[N-:17]=[N+:18]=[N-:19].[Na+].O>CN(C)C=O>[C:1]([O:5][C:6]([N:8]1[CH2:11][CH:10]([N:17]=[N+:18]=[N-:19])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 33557Sodium AzideHCID 10753243Tert-butyl 3-(methanesulfonyloxy)azetidine-1-carboxylate

Product 1

HCID 22242836Tert-butyl 3-azidoazetidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

To a stirred solution of methane sulfonate (930 mg, 3.70 mmol, Example 316) in dimethylformamide (20 mL), sodium azide (962 mg, 14.8 mmol, Aldrich) was added and the mixture was stirred at 90° C. overnight. The mixture was poured into water and extracted with ethyl acetate (5×10 mL) and the extracts were combined, washed with water, brine and dried with sodium sulfate. The solvent was removed to give a clear oil. 710 mg, 97%. The compound was directly used for the next step.

Workup

  1. extractionextracted with ethyl acetate (5×10 mL)
  2. washwashed with water, brine
  3. dry with materialdried with sodium sulfate
  4. customThe solvent was removed
  5. customto give a clear oil

Sources & evidence

ORD record
ord-f657250ff9cf43aab7f3c82985b28eff
Source dataset
uspto-grants-2007_01
Patent number
US07157455B2

Reaction notes

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