Sodium Azide → HCID 86750806, compound

HRID 1779966Notes

Reaction equation

HRID 1779966 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][C@H:6]1[C:11]([O:12][CH3:13])=[N:10][C@H:9]([CH:14]([CH3:16])[CH3:15])[C:8]([O:17][CH3:18])=[N:7]1.[N-:19]=[N+:20]=[N-:21].[Na+]>CN(C=O)C.O>[N:19]([CH2:2][CH2:3][CH2:4][CH2:5][C@H:6]1[C:11]([O:12][CH3:13])=[N:10][C@H:9]([CH:14]([CH3:16])[CH3:15])[C:8]([O:17][CH3:18])=[N:7]1)=[N+:20]=[N-:21]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 57307329HCID 57307329, compound

Product 1

HCID 86750806HCID 86750806, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

1-Bromo-4-[(2R,5S)-3,6-dimethoxy-2-isopropyl-2,5-dihydro-5-pyrazinyl]-butane (3.81 g, 11.95 mmol) were dissolved in 40 ml DMF and 3.25 g NaN3 (50 mmol) and 0.1 g NBu4I were added. The solution was kept between 70° and 80° C. overnight and diluted with 50 ml water. After extraction with chloroform the organic layers were collected and dried (MgSO4). The residue was purified by flash chromatography (hexane/ethyl acetate 9/1).

Workup

  1. extractionAfter extraction with chloroform the organic layers
  2. customwere collected
  3. dry with materialdried (MgSO4)
  4. customThe residue was purified by flash chromatography (hexane/ethyl acetate 9/1)

Sources & evidence

ORD record
ord-174f7be2114b4b20a9769754c3f8e35f
Source dataset
uspto-grants-1997_05
Patent number
US05629293

Reaction notes

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