Cyclopentanol → HCID 22032982, compound

HRID 2221278Notes

Reaction equation

HRID 2221278 reaction equation
C1(S([N:10]2[C:18]3[C:13](=[CH:14][C:15]([C:19]4[CH:24]=[CH:23][CH:22]=[C:21]([Cl:25])[CH:20]=4)=[CH:16][CH:17]=3)[CH:12]=[CH:11]2)(=O)=O)C=CC=CC=1.[CH:26]1(O)[CH2:30][CH2:29][CH2:28][CH2:27]1.CC([O-])(C)C.[K+]>C1(C)C=CC=CC=1.C1COCC1.[Cl-].[Na+].O>[Cl:25][C:21]1[CH:20]=[C:19]([C:15]2[CH:14]=[C:13]3[C:18](=[CH:17][CH:16]=2)[N:10]([CH:26]2[CH2:30][CH2:29][CH2:28][CH2:27]2)[CH:11]=[CH:12]3)[CH:24]=[CH:23][CH:22]=1

Participants

7

Reactant 3

HCID 7298CyclopentanolHCID 22032912HCID 22032912, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 22032982HCID 22032982, compound

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
150 °C

Procedure

A 5 mL conical glass microwave reaction vessel with stir bar, sealed with a septum and swept with nitrogen, was charged with a solution of 0.08 g (0.22 mmol) 1-(benzenesulfonyl-5-(3-chlorophenyl)-1H-indole in 1.2 mL anhydrous toluene. 32 μL (0.33 mmol) cyclopentanol was added with stirring, followed by 0.3 mL 1.0M solution of KOt-Bu in THF. The septum was removed and the vial was sealed with a cap. The reaction vessel was heated to 150° C. for 350 seconds in a microwave reactor (Personal Chemistry Inc., Milford, Mass.) and allowed to cool to room temperature. An aliquot removed for LC analysis indicated that the reaction was complete. The crude reaction mixture was taken up in 10 mL of brine and extracted with EtOAc. The organic phase was filtered through an 8 mL aqueous/organic separation column (Alltech Associates, Inc., Deerfield, Ill.) and was concentrated. The residue was purified by RP-HPLC (see Note 1 below) to give 11.2 mg 5-(3-chlorophenyl)-1-cyclopentyl-1H-indole as an oil.

Workup

  1. customsealed with a septum
  2. stirringwith stirring
  3. customThe septum was removed
  4. customthe vial was sealed with a cap
  5. temperatureto cool to room temperature
  6. customAn aliquot removed for LC analysis
  7. customThe crude reaction mixture
  8. extractionextracted with EtOAc
  9. filtrationThe organic phase was filtered through an 8 mL aqueous/organic separation column (Alltech Associates, Inc., Deerfield, Ill.)
  10. concentrationwas concentrated
  11. customThe residue was purified by RP-HPLC (see Note 1 below)

Sources & evidence

ORD record
ord-2456858095cd456ea536255d1dcb29a1
Source dataset
uspto-grants-2008_05
Patent number
US07368471B2

Reaction notes

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