Sodium Azide → HCID 14261123, compound

HRID 1085666Notes

Reaction equation

HRID 1085666 reaction equation
Br[C@H:2]([CH2:12][CH:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1)[C@H:3]1[O:8][C:6](=[O:7])[C@H:5]([CH:9]([CH3:11])[CH3:10])[CH2:4]1.[N-:19]=[N+:20]=[N-:21].[Na+]>>[N:19]([C@@H:2]([CH2:12][CH:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1)[C@H:3]1[O:8][C:6](=[O:7])[C@H:5]([CH:9]([CH3:11])[CH3:10])[CH2:4]1)=[N+:20]=[N-:21]

Participants

3

Reactant 2

HCID 33557Sodium AzideHCID 11034458HCID 11034458, compound

Product 1

HCID 14261123HCID 14261123, compound

Procedure

42.5 g (0.135 mol) of 5(R)-bromo-6-cyclohexyl-2(S)-isopropyl-4(S)-hexanolide and 35 g (0.54 mol of NaN3 in 480 ml of N,N'-dimethyl-N,N'-propylene urea (DMPU) are stirred at room temperature for 72 hours and then poured onto 1 liter of ice-cold 0.1N HCl. The mixture is then extracted three times with ether, and the combined organic phases are washed twice with 0.1N HCl and three times with brine and dried with MgSO4. After concentrating the solvent by evaporation, the residue is recrystallised from hexane: m.p. 38.5°-39°.

Workup

  1. extractionThe mixture is then extracted three times with ether
  2. washthe combined organic phases are washed twice with 0.1N HCl and three times with brine
  3. dry with materialdried with MgSO4
  4. concentrationAfter concentrating the solvent
  5. customby evaporation
  6. customthe residue is recrystallised from hexane

Sources & evidence

ORD record
ord-482a445d49344d4ca2ca32f10fdc8592
Source dataset
uspto-grants-1991_04
Patent number
US05010189

Reaction notes

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