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

HRID 1453214Notes

Reaction equation

HRID 1453214 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). 1H NMR (CDCl3): δ 1.43-1.80 (bm, 8H), 2.20 (m, 2H), 2.24 (m, 1H), 2.72 (m, 2H), 3.06 (m, 3H), 3.30 (m, 1H), 3.76 (m, 4H), 6.72 (d, J=8.64 Hz, 2H), 6.78 (d, J=8.64 Hz, 2H), 6.94 (m, 3H), 7.23 (m, 2H). Exact Mass: Calcd, 406.51; Found, 406.21.

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-06b37670faf045b4a01829b29a6b6bf7
Source dataset
uspto-grants-2009_01
Patent number
US07473790B2

Reaction notes

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