Methyl iodide → HCID 16076112, compound

HRID 1453329Notes

Reaction equation

HRID 1453329 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:10][CH2:11][C:12]2([CH:20]3[CH2:24][CH2:23][CH2:22][CH2:21]3)[O:17][C:16](=[O:18])[CH2:15][C:14](=[O:19])[CH2:13]2)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].[CH2:25]1CCN2C(=NCCC2)CC1.IC>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:10][CH2:11][C:12]2([CH:20]3[CH2:24][CH2:23][CH2:22][CH2:21]3)[O:17][C:16](=[O:18])[CH:15]=[C:14]([O:19][CH3:25])[CH2:13]2)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 160761096-(3-chloro-4-methoxyphenethyl)-6-cyclopentyl-dihydro-3H-pyran-2,4-dione

Product 1

HCID 16076112HCID 16076112, compoundYield 13.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 6-[2-(3-Chloro-4-methoxy-phenyl)-ethyl]-6-cyclopentyl-dihydro-pyran-2,4-dione (60 mg, 0.17 mmol) from Example B(87), dissolved in DMF (1.5 mL), were added DBU (0.028 mL, 0.188 mmol) and iodomethane (0.011 mL, 0.17 mmol). The reaction was stirred at room temperature overnight, and then was quenched with water. The reaction was extracted with EtOAc, and the organic layers were combined. After washing with saturated NaCl, the organic layer was dried over Na2SO4. The solids were removed by filtration, and the liquid was concentrated by rotary evaporation. Purification by preparatory HPLC gave the desired product (8.2 mg, 13% yield). 1H NMR (CDCl3) δ: 1.47-1.69 (m, 8H), 1.89-1.95 (m, 2H), 2.25-2.35 (m, 2H), 2.52-2.63 (m, 3H), 3.67 (s, 3H), 3.80 (s, 3H), 6.77 (d, J=8.32 Hz, 1H), 6.94 (dd, J1=8.32 Hz, J2=2.24 Hz, 1H), 7.09 (d, J=1.92 Hz, 1H).

Workup

  1. customwas quenched with water
  2. extractionThe reaction was extracted with EtOAc
  3. washAfter washing with saturated NaCl
  4. dry with materialthe organic layer was dried over Na2SO4
  5. customThe solids were removed by filtration
  6. concentrationthe liquid was concentrated by rotary evaporation
  7. customPurification by preparatory HPLC

Sources & evidence

ORD record
ord-6dab224c423d44cfbdf09819c43cbffd
Source dataset
uspto-grants-2009_01
Patent number
US07473790B2

Reaction notes

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