(4aS,8aR)-4a-(3-Methoxyphenyl)-2-methyloctahydroisoquinolin-6(2H)-one → Ammonium Hydroxide

HRID 1739776Notes

Reaction equation

HRID 1739776 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C@@:9]23[CH2:18][C:17](=[O:19])[CH2:16][CH2:15][C@H:14]2[CH2:13][N:12]([CH3:20])[CH2:11][CH2:10]3)[CH:6]=[CH:7][CH:8]=1.[C:21]1([Li])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>CCOCC.C1COCC1.C1C=CC=CC=1>[NH4+:12].[OH-:2].[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C@@:9]23[CH2:18][C:17]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)([OH:19])[CH2:16][CH2:15][C@H:14]2[CH2:13][N:12]([CH3:20])[CH2:11][CH2:10]3)[CH:6]=[CH:7][CH:8]=1

Participants

7

Reactant 2

HCID 12906774(4aS,8aR)-4a-(3-Methoxyphenyl)-2-methyloctahydroisoquinolin-6(2H)-oneHCID 178506676HCID 178506676, compound

Product 2

HCID 14923Ammonium HydroxideHCID 86754617HCID 86754617, compound

Reagents, catalysts & solvents 3

HCID 241BenzeneSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1.1 g (0.04 mol) of (±)-trans-1,2,3,4,4a,5,6,7,8,8a-decahydro4a-(3-methoxyphenyl)-2-methyl-6-isoquinolinone in 50 ml of Et2O and 50 ml of dry THF, under a nitrogen atmosphere and at 0° C., 10.3 ml (0.02 mol) of a 2.0 M solution of phenyllithium in benzene were added dropwise. The reaction mixture was allowed to warm up to room temperature overnight, then it was quenched with a saturated NH4Cl solution. The aqueous phase was extracted with AcOEt, then the combined organic phases were washed with a saturated NaCl solution and dried over Na2SO4. The solvent was removed in vacuo and the residue was purified by flash chromatography, eluting with a mixture CH2Cl2 /MeOH/conc. NH4OH 86:10:0.6 respectively, yielding 0.65 g of the title compound.

Workup

  1. customit was quenched with a saturated NH4Cl solution
  2. extractionThe aqueous phase was extracted with AcOEt
  3. washthe combined organic phases were washed with a saturated NaCl solution
  4. dry with materialdried over Na2SO4
  5. customThe solvent was removed in vacuo
  6. customthe residue was purified by flash chromatography
  7. washeluting with a mixture CH2Cl2 /MeOH/conc

Sources & evidence

ORD record
ord-f4f0ec8ab4684877808097cfc7241c55
Source dataset
uspto-grants-1999_10
Patent number
US05968949

Reaction notes

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