Sodium Azide → tert-butyl ((3S,4S)-4-azidotetrahydro-2H-pyran-3-yl)carbamate

HRID 56398Notes

Reaction equation

HRID 56398 reaction equation
CS(O[C@@H:6]1[CH2:11][CH2:10][O:9][CH2:8][C@H:7]1[NH:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])(=O)=O.[N-:20]=[N+:21]=[N-:22].[Na+].C([O-])(=O)C.[Na+]>CN(C=O)C>[N:20]([C@H:6]1[CH2:11][CH2:10][O:9][CH2:8][C@H:7]1[NH:12][C:13](=[O:14])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[N+:21]=[N-:22]

Participants

5

Reactant 3

HCID 33557Sodium AzideHCID 517045Sodium AcetateHCID 118036785D-threo-Pentitol, 1,5-anhydro-2,4-dideoxy-2-[[(1,1-dimethylethoxy)carbonyl]amino]-, 3-methanesulfonate

Product 1

HCID 118041477tert-butyl ((3S,4S)-4-azidotetrahydro-2H-pyran-3-yl)carbamateYield 100%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
95 °C

Procedure

(3R,4R)-3-((tert-butoxycarbonyl)amino)tetrahydro-2H-pyran-4-yl methanesulfonate (2.2 g, 7.45 mmol), sodium azide (0.968 g, 14.90 mmol) and sodium acetate (1.222 g, 14.90 mmol) were taken up in DMF (15 ml). The reaction mixture was heated to 95° C. overnight. The reaction mixture was removed from heat and 20 ml of water was added and stirred while cooling. The reaction mixture was extracted with EtOAc. The organic layers were combined and washed with water. The organics were dried and solvent removed to give tert-butyl ((3S,4S)-4-azidotetrahydro-2H-pyran-3-yl)carbamate (1.8 g, 7.43 mmol, 100% yield) as a yellow oil. MS (ES+) C10H18N4O3 requires: 242, found: 265 [M+Na]+.

Workup

  1. customThe reaction mixture was removed
  2. temperaturefrom heat
  3. addition20 ml of water was added
  4. temperaturewhile cooling
  5. extractionThe reaction mixture was extracted with EtOAc
  6. washwashed with water
  7. customThe organics were dried
  8. customsolvent removed

Sources & evidence

ORD record
ord-b686d07aa7fa4898810dfb27a3f7ac5c
Source dataset
uspto-grants-2016_09
Patent number
US09434700B2

Reaction notes

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