Potassium Carbonate → HCID 57907640, compound

HRID 887101Notes

Reaction equation

HRID 887101 reaction equation
CO[C:3]1[CH2:4][CH2:5][CH:6]([C:8]([O:10][CH3:11])=[O:9])[N:7]=1.[N-:12]=[N+:13]=[N-:14].[Na+].C(=O)([O-])[O-].[K+].[K+]>C(O)(=O)C.C(OCC)C>[N:12]1[N:13]=[N:14][N:7]2[CH:6]([C:8]([O:10][CH3:11])=[O:9])[CH2:5][CH2:4][C:3]=12

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 33557Sodium AzideHCID 15924113137131-35-2

Product 1

HCID 57907640HCID 57907640, compoundYield 31%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of starting methyl 5-methoxy-3,4-dihydro-2H-pyrrole-2-carboxylate (900 mg, 6.04 mmol) in 4 mL of acetic acid was added sodium azide (975 mg, 12.08 mmol) and the resulting suspension heat to 60° C. and stirred vigorously for 48 h. The solution was cooled to room temperature and diluted with 35 mL of ethyl ether. Solid potassium carbonate was added to the solution which was stirred at room temperature for 20 min. The solids were filtered off via fritted funnel, washed with cool ethyl ether and concentrated under vacuum. Solid precipitated during concentration and was filtered off after concentrating to one-fifth volume. The solids were washed once with cold ether (3 mL) and dried under high vacuum overnight to afford the title compound (308 mg, 31%). LC-MS: m/z (ES)=169 (MH)+.

Workup

  1. temperatureThe solution was cooled to room temperature
  2. stirringwas stirred at room temperature for 20 min
  3. filtrationThe solids were filtered off via fritted funnel
  4. washwashed with cool ethyl ether
  5. concentrationconcentrated under vacuum
  6. customSolid precipitated during concentration
  7. filtrationwas filtered off
  8. concentrationafter concentrating to one-fifth volume
  9. washThe solids were washed once with cold ether (3 mL)
  10. customdried under high vacuum overnight

Sources & evidence

ORD record
ord-20e3816dbe934788bf7a884cf2145890
Source dataset
uspto-grants-2012_08
Patent number
US08247415B2

Reaction notes

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