Water → 1-Benzyl-3,4-dihydro-2(1H)-quinolone-3-spirocyclopentane

HRID 649200

Reaction equation

HRID 649200 reaction equation
CN(C)P(N(C)C)(N(C)C)=O.[CH2:12]([N:19]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH2:22][CH2:21][C:20]1=[O:29])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.Cl[CH2:31][CH2:32][CH2:33][CH2:34]I.O>O1CCCC1>[CH2:12]([N:19]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH2:22][C:21]2([CH2:34][CH2:33][CH2:32][CH2:31]2)[C:20]1=[O:29])[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 12679HexamethylphosphoramideHCID 825271-Chloro-4-iodobutaneHCID 28074572(1H)-Quinolinone, 3,4-dihydro-1-(phenylmethyl)-

Product 1

HCID 704193281-Benzyl-3,4-dihydro-2(1H)-quinolone-3-spirocyclopentane

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-22 °C

Procedure

To diethylamine (0.96 ml, 0.0092 mol) in 4 ml tetrahydrofuran at 0° C. was added butyllithium (5.8 ml of 1.6 M in hexane, 0.0092 mol) and the mixture stirred for 10 minutes at 0° C., then warmed to room temperature, thus forming a solution of lithium diethylimide. The solution was cooled to -22° C., hexamethylphosphoramide (4 ml) and then, over a 5 minutes period, 1-benzyl-3,4-dihydro-2(1H)-quinolone (1.0 g, 0.0042 mol) in 6 ml tetrahydrofuran were added, and the resulting mixture warmed to 15° C. over 1 hour, then recooled to -55° C., at which point a solution of 1-chloro-4-iodobutane (0.95 g, 1.03 molar equivalents) in 10 ml tetrahydrofuran was added over 5 minutes. After stirring 16 hours at -55° C., water (5 ml) was added and the mixture warmed to room temperature, poured into 30 ml H2O and extracted 3×15 ml ether. The organic layers wre combined, washed 4×20 ml H2O, dried (MgSO4) and stripped to dryness (1.32 g) and radially chromatographed on a thick layer plate of silica gel with CHCl3 as eluant to produce present title product, 0.48 g; mass spectra includes molecular ion at 291.

Workup

  1. temperaturethe resulting mixture warmed to 15° C. over 1 hour
  2. customrecooled to -55° C., at which point
  3. additionwas added over 5 minutes
  4. temperaturethe mixture warmed to room temperature
  5. extractionextracted 3×15 ml ether
  6. washwashed 4×20 ml H2O
  7. dry with materialdried (MgSO4)
  8. customradially chromatographed on a thick layer plate of silica gel with CHCl3 as eluant

Sources & evidence

ORD record
ord-38a291e6e1f14ae484fa240a874013bc
Source dataset
uspto-grants-1988_04
Patent number
US04738972

Linked notes

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