Sodium hydride → HCID 54522152, compound

HRID 1265255Notes

Reaction equation

HRID 1265255 reaction equation
[CH3:1][C:2]1([CH3:18])[C:7]2[CH:8]=[C:9]3[C:14](=[CH:15][C:6]=2[C:5]([CH3:17])([CH3:16])[CH2:4][CH2:3]1)[NH:13][CH2:12][CH2:11][CH2:10]3.[H-].[Na+].Br[CH2:22][C:23]1[CH:32]=[CH:31][C:26]([C:27]([O:29][CH3:30])=[O:28])=[CH:25][CH:24]=1>C1COCC1>[CH3:30][O:29][C:27](=[O:28])[C:26]1[CH:31]=[CH:32][C:23]([CH2:22][N:13]2[C:14]3[C:9](=[CH:8][C:7]4[C:2]([CH3:18])([CH3:1])[CH2:3][CH2:4][C:5]([CH3:17])([CH3:16])[C:6]=4[CH:15]=3)[CH2:10][CH2:11][CH2:12]2)=[CH:24][CH:25]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 256687Methyl 4-(bromomethyl)benzoateHCID 18615010HCID 18615010, compound

Product 1

HCID 54522152HCID 54522152, compoundYield 40.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
60 °C

Procedure

To a solution of 6,6,9,9-tetramethyl-1,2,3,4,6,7,8,9-octahydrobenzo[g]quinoline (200 mg, 0.823 mmol) in THF (4 mL) was added NaH (30 mg, 1.2 mmol) in one portion at ambient temperature. To this solution was added methyl 4-(bromomethyl)-benzoate (377 mg, 1.6 mmol) in THF (8 mL). The mixture was then heated at 60° C. for 8 h, cooled to ambient temperature, quenched with aqueous saturated NH4Cl (20 mL), extracted with EtOAc (100 mL), dried (MgSO4), concentrated, and purified by column chromatography (10% ether in hexanes) to afford 4-(6,6,9,9-tetramethyl-3,4,6,7,8,9-hexahydro-2H-benzo[g]quinolin-1-ylmethyl)-benzoic acid methyl ester 130 mg (40%): 1H NMR (400 MHz, CDCl3) δ 7.98(½ ABq, 2H, J=9.0 Hz, ArH), 7.38(½ ABq, 2H, J=9.0 Hz, ArH), 6.91(s, 1H, ArH), 6.3(s, 1H, ArH) 4.45(s, 2H, CH2), 3.90(s, 3H, CH3), 3.2(t, 2H, J=5.4 Hz, ring CH2), 2.79(t, 2H, J=6.4 Hz, ring CH2), 2.02(m, 2H, ring CH2), 1.59(s, 4H, 2CH2), 1.22(s, 6H, 2CH3), 1.06(s, 6H, 2CH3).

Workup

  1. temperaturecooled to ambient temperature
  2. customquenched with aqueous saturated NH4Cl (20 mL)
  3. extractionextracted with EtOAc (100 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. custompurified by column chromatography (10% ether in hexanes)

Sources & evidence

ORD record
ord-3d897943a0ad4318b269ae00e5a32e23
Source dataset
uspto-grants-2003_04
Patent number
US06545049B1

Reaction notes

Loading…