Cesium carbonate → {2-[2-(2-Fluoro-ethyl)-2H-tetrazol-5-yl]-ethyl}-carbamic acid tert-butyl ester

HRID 1672512Notes

Reaction equation

HRID 1672512 reaction equation
[C:1]([O:5][C:6](=[O:15])[NH:7][CH2:8][CH2:9][C:10]1[N:11]=[N:12][NH:13][N:14]=1)([CH3:4])([CH3:3])[CH3:2].C([O-])([O-])=O.[Cs+].[Cs+].Br[CH2:23][CH2:24][F:25]>CN(C=O)C>[C:1]([O:5][C:6](=[O:15])[NH:7][CH2:8][CH2:9][C:10]1[N:11]=[N:12][N:13]([CH2:23][CH2:24][F:25])[N:14]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 129822-Fluoroethyl bromideHCID 19938452[2-(1H-Tetrazol-5-yl)-ethyl]carbamic acid tert-butyl ester

Product 1

HCID 57466829{2-[2-(2-Fluoro-ethyl)-2H-tetrazol-5-yl]-ethyl}-carbamic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of [2-(2H-Tetrazol-5-yl)-ethyl]-carbamic acid tert-butyl ester 0.45 g, 2.11 mmol) in dry DMF (14 ml) was suspended Cs2CO3 (0.825 g, 2.53 mmol) and the reaction mixture stirred for 15 minutes. 1-Bromo-2-fluoroethane (0.63 ml, 8.44 mmol) was added and the reaction mixture stirred at ambient temperature for 5 hours. The reaction mixture was filtered and the DMF evaporated to afford the crude product as a brown oil. The crude material was absorbed onto silica and purified by silica chromatography eluting with a gradient of 3:1 to 2:1 Ethylacetate:hexane to afford the titled product as a colorless oil.

Workup

  1. stirringthe reaction mixture stirred at ambient temperature for 5 hours
  2. filtrationThe reaction mixture was filtered
  3. customthe DMF evaporated
  4. customto afford the crude product as a brown oil
  5. customThe crude material was absorbed onto silica
  6. custompurified by silica chromatography
  7. washeluting with a gradient of 3:1 to 2:1 Ethylacetate

Sources & evidence

ORD record
ord-28eb8f7211af4ad68366afde85475c0d
Source dataset
uspto-grants-2011_08
Patent number
US07998990B2

Reaction notes

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