Sodium Azide → (s)-Tert-butyl 2-(azidomethyl)morpholine-4-carboxylate

HRID 574876Notes

Reaction equation

HRID 574876 reaction equation
S(O[CH2:12][C@H:13]1[O:18][CH2:17][CH2:16][N:15]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:14]1)(C1C=CC(C)=CC=1)(=O)=O.[N-:26]=[N+:27]=[N-:28].[Na+]>CN(C)C=O>[N:26]([CH2:12][C@H:13]1[O:18][CH2:17][CH2:16][N:15]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:14]1)=[N+:27]=[N-:28]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 54043638(S)-tert-Butyl 2-((tosyloxy)methyl)morpholine-4-carboxylate

Product 1

HCID 90413392(s)-Tert-butyl 2-(azidomethyl)morpholine-4-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of EXAMPLE 258A (1.66 g) and sodium azide (0.581 g) in anhydrous N,N-dimethylformamide (10 mL) was stirred at 90° C. for 4 hours. The mixture was cooled and concentrated to dryness. The residue was taken up in 5% aqueous sodium carbonate solution and extracted with methylene chloride. The organic solution was dried (MgSO4), filtered and concentrated to give a solid.

Workup

  1. temperatureThe mixture was cooled
  2. concentrationconcentrated to dryness
  3. extractionextracted with methylene chloride
  4. dry with materialThe organic solution was dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give a solid

Sources & evidence

ORD record
ord-2eed67968df44f9cbc4030ba9c88cfd4
Source dataset
uspto-grants-2015_05
Patent number
US09034875B2

Reaction notes

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