Tetrahydrofuran → HCID 18333060, compound

HRID 2269761Notes

Reaction equation

HRID 2269761 reaction equation
[Li+].CC([N-]C(C)C)C.C1COCC1.[CH3:14][N:15]([CH2:17][CH:18]1[CH2:27][C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[N:20]([S:28]([CH3:31])(=[O:30])=[O:29])[CH2:19]1)[CH3:16].[C:32]1([C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[CH:37]=[CH:36][C:35]([CH2:38]Br)=[CH:34][CH:33]=1>O>[C:32]1([C:40]2[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=2)[CH:33]=[CH:34][C:35]([CH2:38][CH2:31][S:28]([N:20]2[C:21]3[C:26](=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH2:27][CH:18]([CH2:17][N:15]([CH3:14])[CH3:16])[CH2:19]2)(=[O:29])=[O:30])=[CH:36][CH:37]=1

Participants

6

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 2577161,1'-Biphenyl, 4-(bromomethyl)-HCID 2724682Lithium diisopropylamideHCID 18333022HCID 18333022, compound

Product 1

HCID 18333060HCID 18333060, compoundYield 10.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

LDA (1.9 M/THF, 1.2 ml) was added dropwise to a THF solution of 3-(N,N-dimethylamino)methyl-1-methylsufonyl-1,2,3,4-tetrahydroquinoline (0.24 g). The reaction mixture was stirred under ice-cooling for 30 minutes. A THF (1 ml) solution of 4-biphenylylmethyl bromide (0.16 g) was added to the reaction mixture, which was stirred at room temperature for 3 hours. Water was added to the reaction mixture, which was extracted with ethyl acetate. The organic layer was washed with water, Lil then dried and concentrated. The residue was purified by silica gel column chromatography (eluent: ethyl acetate), which was further recrystallized from hexane-ethyl acetate to give the entitled compound (30 mg).

Workup

  1. temperaturecooling for 30 minutes
  2. stirringwas stirred at room temperature for 3 hours
  3. extractionwas extracted with ethyl acetate
  4. washThe organic layer was washed with water, Lil
  5. customthen dried
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel column chromatography (eluent: ethyl acetate), which
  8. customwas further recrystallized from hexane-ethyl acetate

Sources & evidence

ORD record
ord-14493211dab846488f4887dc4d348d99
Source dataset
uspto-grants-2001_12
Patent number
US06329389B1

Reaction notes

Loading…