Dimethylformamide → HCID 85966059, compound

HRID 1822805Notes

Reaction equation

HRID 1822805 reaction equation
S([O-])(=O)(=O)[CH3:2].[N-]=[N+:7]=[N-:8].[Na+].C[N:11]([CH:13]=O)C.[CH3:15][C:16](=O)[O:17][CH2:18][CH3:19]>>[N:11]([CH2:13][CH2:2][CH:15]1[CH2:19][CH2:18][O:17][CH2:16]1)=[N+:7]=[N-:8]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 8857Ethyl AcetateHCID 33557Sodium AzideHCID 85257Methanesulfonate

Product 1

HCID 85966059HCID 85966059, compoundYield 75%

Conditions

Temperature
80 °C

Procedure

The crude mesylate (2.03 g, 10 mM), sodium azide (3.25 g, 50 mM) and DMF were combined and heated at 80° C. for 2 hr, cooled to rt then the mixture was diluted with EA and thoroughly washed with water (3×100 mL) and brine. The organics were dried, filtered and concentrated then passed through a short silica gel column eluted with 30% ethyl acetate/hexanes to yield 3-(2-azido-ethyl) tetrahydro-furan (1.04 g, 75%). A catalytic amount of 10% palladium on carbon was added to a methanolic solution of the azide (1.04 g, 7.5 mM), the reaction flask was then briefly evacuated under house vacuum and H2 was added via a balloon. The reaction was stirred at rt overnight under an atmosphere of H2, filtered through a plug of celite, which was thoroughly rinsed with MeOH. One molar HCl in Et2O (10 mL) was added then the volatiles were removed to give 2-(cyclopentyl)ethylamine as the HCl salt (51% yield). ESI-MS (m/z) 114 [M+H]+.

Workup

  1. temperaturecooled to rt
  2. washthoroughly washed with water (3×100 mL) and brine
  3. customThe organics were dried
  4. filtrationfiltered
  5. concentrationconcentrated
  6. washeluted with 30% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-e58a477d363344e4bbd4452bd05d7c74
Source dataset
uspto-grants-2006_05
Patent number
US07037916B2

Reaction notes

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