5-[(Benzylamino)methyl]cyclohex-2-en-1-ol → 6-Benzyl-6-azabicyclo[3.2.1]octan-3-one

HRID 597965Notes

Reaction equation

HRID 597965 reaction equation
[CH2:1]([NH:8][CH2:9][CH:10]1[CH2:15][CH:14]([OH:16])[CH:13]=[CH:12][CH2:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>ClCCl.[O-2].[O-2].[Mn+4]>[CH2:1]([N:8]1[CH2:9][CH:10]2[CH2:11][CH:12]1[CH2:13][C:14](=[O:16])[CH2:15]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 150646815-[(Benzylamino)methyl]cyclohex-2-en-1-ol

Product 1

HCID 574857466-Benzyl-6-azabicyclo[3.2.1]octan-3-oneYield 69%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-(benzylaminomethyl)cyclohex-2-enol (3.80 g, 17.5 mmol) in dry dichloromethane (150 ml) was added activated manganese dioxide (18.0 g, 210 mmol) in one portion. The mixture was stirred vigorously under nitrogen for 2 h. The yellow solution was filtered through Celite and the solids were washed with dichloromethane (2×50 ml). The combined filtrates were concentrated by rotary evaporation to give an orange oil, which solidified on brief standing. The solid was recrystallized from hot hexane/ether to afford the ketone as an off-white solid (2.6 g, 68%).

Workup

  1. filtrationThe yellow solution was filtered through Celite
  2. washthe solids were washed with dichloromethane (2×50 ml)
  3. concentrationThe combined filtrates were concentrated by rotary evaporation
  4. customto give an orange oil, which
  5. customThe solid was recrystallized from hot hexane/ether

Sources & evidence

ORD record
ord-82ea890961434819b751ca53d6f378cd
Source dataset
uspto-grants-2011_03
Patent number
US07897611B2

Reaction notes

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