Sodium Iodide → 3-Benzyl-6-cyclopentyl-6-[2-(4-methoxyphenyl)ethyl]tetrahydropyran-2,4-dione

HRID 858760Notes

Reaction equation

HRID 858760 reaction equation
C1CCN2C(=NCCC2)CC1.[CH:12]1([C:17]2([CH2:25][CH2:26][C:27]3[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=3)[O:22][C:21](=[O:23])[CH2:20][C:19](=[O:24])[CH2:18]2)[CH2:16][CH2:15][CH2:14][CH2:13]1.[CH2:35](Br)[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1.[I-].[Na+]>C1C=CC=CC=1>[CH2:35]([CH:20]1[C:19](=[O:24])[CH2:18][C:17]([CH:12]2[CH2:16][CH2:15][CH2:14][CH2:13]2)([CH2:25][CH2:26][C:27]2[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=2)[O:22][C:21]1=[O:23])[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 7498Benzyl BromideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 160761026-(4-methoxyphenethyl)-6-cyclopentyl-dihydro-3H-pyran-2,4-dione

Product 1

HCID 167288493-Benzyl-6-cyclopentyl-6-[2-(4-methoxyphenyl)ethyl]tetrahydropyran-2,4-dioneYield 12.7%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

DBU (28.6 ul, 0.191 mmol) was added to a solution of 6-cyclopentyl-6-[2-(4-methoxyphenyl)ethyl]dihydro-2H-pyran-2,4(3H)-dione (55 mg, 0.174 mmol, described below) in benzene (1.9 ml), under an atmosphere of argon. Benzyl bromide (21 ul, 0.174 mmol) was then added. The reaction mixture was stirred at room temperature for 20 minutes, followed by the addition of 5 crystals of sodium iodide. The reaction mixture was stirred for a further 24 hrs, after which time the mixture was filtered through a plug of Celite. The filtrate was concentrated in vacuo and the residue purified by prep HPLC to afford the title compound as a white solid (9.0 mg).

Workup

  1. stirringThe reaction mixture was stirred for a further 24 hrs
  2. filtrationafter which time the mixture was filtered through a plug of Celite
  3. concentrationThe filtrate was concentrated in vacuo
  4. customthe residue purified by prep HPLC

Sources & evidence

ORD record
ord-af6972a4569a4c22877022462b2e6f6e
Source dataset
uspto-grants-2006_12
Patent number
US07148226B2

Reaction notes

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