Benzaldehyde → HCID 86754620, compound

HRID 1739779Notes

Reaction equation

HRID 1739779 reaction equation
CC([O-:5])(C)C.[K+].[CH3:7][O:8][C:9]1[CH:10]=[C:11]([C@@:15]23[CH2:24][C:23](=[O:25])[CH2:22][CH2:21][C@H:20]2[CH2:19][N:18]([CH3:26])[CH2:17][CH2:16]3)[CH:12]=[CH:13][CH:14]=1.[CH:27](=O)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>C1COCC1>[NH4+:18].[OH-:5].[CH:27](=[C:22]1[CH2:21][C@@H:20]2[C@:15]([C:11]3[CH:12]=[CH:13][CH:14]=[C:9]([O:8][CH3:7])[CH:10]=3)([CH2:16][CH2:17][N:18]([CH3:26])[CH2:19]2)[CH2:24][C:23]1=[O:25])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

6

Reactant 3

HCID 240BenzaldehydeHCID 12906774(4aS,8aR)-4a-(3-Methoxyphenyl)-2-methyloctahydroisoquinolin-6(2H)-oneHCID 23665647Potassium tert-butoxide

Product 2

HCID 14923Ammonium HydroxideHCID 86754620HCID 86754620, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
10 °C

Procedure

0.96 g (8.6 mmol) of t-BuOK were suspended in 100 ml of dry THF under a nitrogen atmosphere, and 1.95 g (7.13 mmol) of (±)-trans-1,2,3,4,4a,5,6,7,8,8a-decahydro4a-(3-methoxyphenyl)-2-methyl-6-isoquinolinone dissolved in 50 ml of dry THF were added at -10° C. The temperature was allowed to warm to 10° C. in 1 h, then the reaction mixture was cooled to -10° C. and 0.87 ml (8.6 mmol) of benzaldehyde dissolved in 25 ml of dry THF were added. The reaction mixture was allowed to warm to room temperature and after 2 h it was poured onto H2O and extracted with AcOEt. The organic phase was dried over Na2SO4 and the solvent removed in vacuo. The residue was purified by flash chromatography, eluting with a mixture CH2Cl2 /MeOH/conc. NH4OH 94.5:5:0.5 respectively, yielding 0.85 g of the title compound.

Workup

  1. additionwere added at -10° C
  2. temperaturethe reaction mixture was cooled to -10° C.
  3. additionwere added
  4. temperatureto warm to room temperature and after 2 h it
  5. additionwas poured onto H2O
  6. extractionextracted with AcOEt
  7. dry with materialThe organic phase was dried over Na2SO4
  8. customthe solvent removed in vacuo
  9. customThe residue was purified by flash chromatography
  10. washeluting with a mixture CH2Cl2 /MeOH/conc

Sources & evidence

ORD record
ord-8badfbfcb91340c9986a048f07a1ce61
Source dataset
uspto-grants-1999_10
Patent number
US05968949

Reaction notes

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