Benzyl Bromide → HCID 57189772, compound

HRID 1490169Notes

Reaction equation

HRID 1490169 reaction equation
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:17][C@H:18]2[CH2:27][CH2:26][C@@H:25]3[C@@H:20]([CH2:21][CH2:22][C:23](=[O:28])[NH:24]3)[CH2:19]2)=[CH:13][CH:12]=1.[OH-].[Na+].C(=O)([O-])[O-].[K+].[K+].S([O-])(O)(=O)=O.[NH4+].[NH4+].[NH4+].[NH4+].S([O-])(O)(=O)=O.S([O-])(O)(=O)=O.S([O-])(O)(=O)=O>C1(C)C=CC=CC=1>[CH3:9][O:10][C:11]1[CH:12]=[CH:13][C:14]([CH2:17][C@H:18]2[CH2:27][CH2:26][C@@H:25]3[C@@H:20]([CH2:21][CH2:22][C:23](=[O:28])[N:24]3[CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH2:19]2)=[CH:15][CH:16]=1

Participants

7

Reactant 5

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 57100403HCID 57100403, compoundHCID 86751477HCID 86751477, compound

Product 1

HCID 57189772HCID 57189772, compoundYield 21.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent3×

Procedure

A solution of benzylbromide (0.44 ml, 0.0037 mol) in toluene (5 ml) was added dropwise to the refluxing mixture of (-)-(4aS,6S,8aR)-3,4,4a,5,6,7,8,8a-octahydro-6-((4-methoxyphenyl)methyl)quinolin-2(1H)-one (0.512 g, 0.0019 mol, prepared according to Example 32), powdered NaOH (0.175 g), potassium carbonate (0.35 g), tetraammonium hydrogen sulphate (0.02 g) and toluene (20 ml). The reaction was refluxed for 4 days. The reaction mixture was then cooled, diluted with toluene and then washed with water. It was then dried over sodium sulphate, filtered and the solvent evaporated. The solid was then chromatographed on a silica gel column in ethylacetate. The first fraction was collected, the solvent evaporated and the resulting solid recrystallised from acetonitrile to give the title compound (0.15 g), mp=118-9° C.; [α]D25 =-10° (1%, CHCl3).

Workup

  1. temperatureThe reaction was refluxed for 4 days
  2. temperatureThe reaction mixture was then cooled
  3. washwashed with water
  4. dry with materialIt was then dried over sodium sulphate
  5. filtrationfiltered
  6. customthe solvent evaporated
  7. customThe solid was then chromatographed on a silica gel column in ethylacetate
  8. customThe first fraction was collected
  9. customthe solvent evaporated
  10. customthe resulting solid recrystallised from acetonitrile

Sources & evidence

ORD record
ord-321c904b391d4249a68936163d3f4c4d
Source dataset
uspto-grants-1997_10
Patent number
US05681839

Reaction notes

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