Ammonia → HCID 58487596, compound

HRID 734378Notes

Reaction equation

HRID 734378 reaction equation
[CH2:1]([N:8]1[CH2:13][CH:12]2[C:10]([C:14]([OH:16])=[O:15])([CH2:11]2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.OS(O)(=O)=O.N.[CH2:23](O)[CH3:24]>>[CH2:23]([O:15][C:14]([C:10]12[CH2:11][CH:12]1[CH2:13][N:8]([CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[CH2:9]2)=[O:16])[CH3:24]

Participants

5

Reactant 4

HCID 222AmmoniaHCID 702EthanolHCID 1118Sulfuric AcidHCID 157134313-Benzyl-3-azabicyclo[3.1.0]hexane-1-carboxylic acid

Product 1

HCID 58487596HCID 58487596, compound

Procedure

To a suspension of 3-benzyl-3-azabicyclo[3.1.0]hexane-1-carboxylic acid (8.5 gm, 0.0390 mole), (prepared as described in EP 0413455A2) in ethyl alcohol (250 ml) was added conc. H2SO4 (10 ml). The resulting pale yellow solution was heated at reflux for 2 hours, cooled to 0° C. and neutralized with aqueous ammonia. The neutralized solution was concentrated and was dissolved in dichloromethane. The organic layer was washed with saturated NaHCO3, water and brine. The organic layer was dried over anhydrous Na2SO4 and was concentrated to give the crude product which was further purified by column chromatography (100-200 mesh, silicagel), eluting the compound with 5% ethyl acetate in hexane to give the pure product as yellow oil.

Workup

  1. temperatureThe resulting pale yellow solution was heated
  2. temperatureat reflux for 2 hours
  3. concentrationThe neutralized solution was concentrated
  4. dissolutionwas dissolved in dichloromethane
  5. washThe organic layer was washed with saturated NaHCO3, water and brine
  6. dry with materialThe organic layer was dried over anhydrous Na2SO4
  7. concentrationwas concentrated
  8. customto give the crude product which
  9. customwas further purified by column chromatography (100-200 mesh, silicagel)
  10. washeluting the compound with 5% ethyl acetate in hexane

Sources & evidence

ORD record
ord-f2bebf234f20439ba3a03b8a4cf3ad56
Source dataset
uspto-grants-2009_09
Patent number
US07592359B2

Reaction notes

Loading…