Benzylamine → 6-Benzyl-6-azabicyclo[3.1.0]hexan-2-one

HRID 81149Notes

Reaction equation

HRID 81149 reaction equation
Br[C:2]1[C:3](=[O:7])[CH2:4][CH2:5][CH:6]=1.[CH2:8]([NH2:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>O.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH2:8]([N:15]1[CH:2]2[CH:6]1[CH2:5][CH2:4][C:3]2=[O:7])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 2

HCID 7504BenzylamineHCID 30146412-Cyclopenten-1-one, 2-bromo-

Product 1

HCID 121197656-Benzyl-6-azabicyclo[3.1.0]hexan-2-one

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolvent

Procedure

To a stirred solution of 2-bromocyclopent-2-enone (1.00 g, 6.21 mmol) in H2O (25 mL), tetrabutylammonium bromide (400 mg, 1.24 mmol) and benzyl amine (790 mg, 7.45 mmol) were added at room temperature. The reaction mixture was stirred for 24 hours and then extracted with EtOAc (100 mL). The organic layer was separated, washed with brine, and dried over anhydrous Na2SO4, filtered and concentrated in vacuo. Purification of the residue on a silica gel column with 0 to 30% EtOAc/Hexanes afforded 6-benzyl-6-azabicyclo[3.1.0]hexan-2-one. MS ESI calc'd. for C12H13NO [M+H]+ 188. found 188.

Workup

  1. extractionextracted with EtOAc (100 mL)
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification of the residue on a silica gel column with 0 to 30% EtOAc/Hexanes

Sources & evidence

ORD record
ord-ce851d7501194615be483279e5640f4c
Source dataset
uspto-grants-2014_09
Patent number
US08846657B2

Reaction notes

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