Acetic acid, azido-, ethyl ester → ethyl[4-(1-hydroxycyclopentyl)-1H-1,2,3-triazol-1-yl]acetate

HRID 82314Notes

Reaction equation

HRID 82314 reaction equation
[N:1]([CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6])=[N+:2]=[N-:3].[OH:10][C:11]1([C:16]#N)[CH2:15][CH2:14][CH2:13][CH2:12]1.O=[C:19]1O[C@H]([C@H](CO)O)C([O-])=C1O.[Na+]>C(O)(C)(C)C.O.S([O-])([O-])(=O)=O.[Cu+2]>[CH2:8]([O:7][C:5](=[O:6])[CH2:4][N:1]1[CH:19]=[C:16]([C:11]2([OH:10])[CH2:15][CH2:14][CH2:13][CH2:12]2)[N:3]=[N:2]1)[CH3:9]

Participants

7

Reactant 3

HCID 69480Acetic acid, azido-, ethyl esterHCID 1998551-HydroxycyclopentanecarbonitrileHCID 23667548Sodium Ascorbate

Product 1

HCID 70847803ethyl[4-(1-hydroxycyclopentyl)-1H-1,2,3-triazol-1-yl]acetateYield 98%

Reagents, catalysts & solvents 3

HCID 24462Copper SulfateCatalystHCID 962WaterSolventHCID 6386tert-ButanolSolvent

Procedure

Ethyl azidoacetate (2.58 g, 20 mmol) was dissolved in tert-butanol (15 mL), and 1-hydroxycyclopentanecarbonitrile (2.20 g, 20 mmol) was added. A solution of sodium ascorbate (0.792 g, 4 mmol) in water (10 mL) followed by a 0.3 M solution of copper sulfate (0.67 mL) was added to the mixture, and stirring continued at room temperature for a further 48 hours. The solution was evaporated to dryness in vacuo and the residue was dissolved in EtOAc (50 mL), dried (MgSO4), filtered and evaporated in vacuo to afford the title compound as green-yellow crystals in 98% yield, 4.69 g. MS m/z 238 [M−H]−

Workup

  1. additionwas added to the mixture
  2. customThe solution was evaporated to dryness in vacuo
  3. dissolutionthe residue was dissolved in EtOAc (50 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-5ba7e8896ee54141a906f80c3a8b6883
Source dataset
uspto-grants-2014_09
Patent number
US08846698B2

Reaction notes

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