Sodium Azide → Tert-butyl 3-azidocyclopentanoate

HRID 1681077Notes

Reaction equation

HRID 1681077 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].S([O-])(=O)(=O)C.S(O[CH:15]1[CH2:19][CH2:18][CH:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16]1)(C)(=O)=O>O>[N:1]([CH:19]1[CH2:15][CH2:16][CH:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:18]1)=[N+:2]=[N-:3]

Participants

5

Reactant 3

HCID 33557Sodium AzideHCID 85257MethanesulfonateHCID 14009993Tert-butyl 3-mesyloxycyclopentanoate

Product 1

HCID 19808143Tert-butyl 3-azidocyclopentanoate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Sodium azide (156 mg) was added to the mesylate [prepared in (1) ]dissolved in hexamethylphosphamide (3 ml). The mixture was poured into water. The mixture was extracted with ethyl acetate. The extract was washed with water, dried over magnesium sulfate and then evaporated to obtain the title compound having the following physical data.

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. washThe extract was washed with water
  3. dry with materialdried over magnesium sulfate
  4. customevaporated

Sources & evidence

ORD record
ord-9e9ebfdaaa1d4977beaff1ebf5a15d0f
Source dataset
uspto-grants-1992_12
Patent number
US05168101

Reaction notes

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