Benzaldehyde → HCID 10453483, compound

HRID 1815683Notes

Reaction equation

HRID 1815683 reaction equation
[C:1]12([CH2:11]S(O)(=O)=O)C(C)(C)[CH:5]([CH2:6][CH2:7]1)[CH2:4][C:2]2=O.[N+:16]([CH2:19][CH2:20][CH2:21][C:22](=[O:26])[CH2:23][CH2:24][CH3:25])([O-:18])=[O:17].C([O:32][CH3:33])(OC)OC.[C:34]([O-])(=O)C.[NH4+:38].[CH:39](=O)[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1>CO>[CH:39](=[N:38][CH:11]([C:1]1[CH:2]=[CH:4][CH:5]=[CH:6][CH:7]=1)[CH:19]([N+:16]([O-:18])=[O:17])[CH2:20][CH2:21][C:22]([O:32][CH3:33])([O:26][CH3:34])[CH2:23][CH2:24][CH3:25])[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1

Participants

7

Reactant 5

HCID 240BenzaldehydeHCID 9005Trimethyl orthoformateHCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-HCID 517165Ammonium AcetateHCID 10920798HCID 10920798, compound

Product 1

HCID 10453483HCID 10453483, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Camphorsulfonic acid is added to a solution of 7-nitro-heptan-4-one from preparation 2 in MeOH and trimethyl orthoformate and the resulting solution is stirred at room temperature for 30 min. A solution of ammonium acetate in MeOH and benzaldehyde is added and the solution is stirred at room temperature for 6 h. The reaction is then heated at 40° C. for 7 h. The reaction is cooled to 35° C. and stirred overnight, then is cooled to 30° C. for 4 h, and finally to room temperature. After stirring over a weekend, the reaction mixture is cooled to 0° C. The product is collected by filtration to afford benzylidene-(5,5-dimethoxy-2-nitro-1phenyl-octyl)-amine with only the cis nitrophenyl stereochemistry.

Workup

  1. temperatureThe reaction is then heated at 40° C. for 7 h
  2. temperatureThe reaction is cooled to 35° C.
  3. stirringstirred overnight
  4. temperatureis cooled to 30° C. for 4 h
  5. customfinally to room temperature
  6. stirringAfter stirring over a weekend
  7. temperaturethe reaction mixture is cooled to 0° C
  8. filtrationThe product is collected by filtration

Sources & evidence

ORD record
ord-74aa79bb9a38475986ca94edcf44b010
Source dataset
uspto-grants-2005_04
Patent number
US06878848B2

Reaction notes

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