Sodium Sulfate → 749934-78-9

HRID 1453332Notes

Reaction equation

HRID 1453332 reaction equation
Cl[CH2:2][CH2:3][C:4]([CH:6]1[CH2:10][CH2:9][CH2:8][CH2:7]1)=[O:5].[N-:11]=[N+]=[N-].[Na+].S([O-])([O-])(=O)=O.[Na+].[Na+].[C:22]([O:29]C(OC(C)(C)C)=O)(=O)[O:23][C:24]([CH3:27])([CH3:26])[CH3:25]>CN(C=O)C>[C:24]([O:23][C:22](=[O:29])[NH:11][CH2:2][CH2:3][C:4]([CH:6]1[CH2:10][CH2:9][CH2:8][CH2:7]1)=[O:5])([CH3:27])([CH3:26])[CH3:25]

Participants

6

Reactant 4

HCID 24436Sodium SulfateHCID 33557Sodium AzideHCID 90495Di-tert-butyl dicarbonateHCID 55298626HCID 55298626, compound

Product 1

HCID 58762663749934-78-9Yield 38%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 3-chloro-1-cyclopentyl-propan-1-one (2.913 g, 18.1 mmol) from Step 1 above in DMF (40 mL) was added sodium azide (1.77 er sodium sulfate, filtered, and concentrated to an oil. The oil was then dissolved in g, 27.2 mmol). The reaction was heated to 70° C. for 3 hours. The reaction was cooled to room temperature, and then diluted with 100 mL of ethyl acetate and 100 mL of water. The layers were separated, and the aqueous was extracted with 2×50 mL of ethyl acetate. The organic layer was then washed with 2×50 mL of water. The organic layer was dried ovethanol (75 mL) and TFA was added (3 mL). To this solution was added 10% Pd/C (300 mg). The slurry was stirred under a hydrogen atmosphere for 2 hours. The solids were removed by filtration, and the organic was concentrated by rotary evaporation to a black oil. The black oil was dissolved in THF (100 mL) and TEA (7.5 mL) and di-tert-butyl pyrocarbonate (1 M in THF, 40 mL, 40 mmol) were added. The reaction was stirred at room temperature for 18 hours, and then concentrated by rotary evaporation. The crude oil was purified by flash chromatography to yield the product (1.677 g, 38%). 1H NMR (CDCl3) δ: 1.43 (s, 9H), 1.56-1.84 (m, 8H), 2.68 (t, J=5.65 Hz, 2H), 2.85 (p, J=5.65 Hz, 1H), 3.36 (q, J=6.03, 2H).

Workup

  1. filtrationfiltered
  2. concentrationconcentrated to an oil
  3. dissolutionThe oil was then dissolved in g, 27.2 mmol)
  4. temperatureThe reaction was cooled to room temperature
  5. additiondiluted with 100 mL of ethyl acetate and 100 mL of water
  6. customThe layers were separated
  7. extractionthe aqueous was extracted with 2×50 mL of ethyl acetate
  8. washThe organic layer was then washed with 2×50 mL of water
  9. dry with materialThe organic layer was dried ovethanol (75 mL) and TFA
  10. additionwas added (3 mL)
  11. additionTo this solution was added 10% Pd/C (300 mg)
  12. customThe solids were removed by filtration
  13. concentrationthe organic was concentrated by rotary evaporation to a black oil
  14. dissolutionThe black oil was dissolved in THF (100 mL)
  15. stirringThe reaction was stirred at room temperature for 18 hours
  16. concentrationconcentrated by rotary evaporation
  17. customThe crude oil was purified by flash chromatography

Sources & evidence

ORD record
ord-800ed66a8336469f8449210949ffdb64
Source dataset
uspto-grants-2009_01
Patent number
US07473790B2

Reaction notes

Loading…