Methyl iodide → HCID 131729316, compound

HRID 657153Notes

Reaction equation

HRID 657153 reaction equation
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[CH2:12][C@H:13]1[CH2:18][C@@H:17]([OH:19])[CH2:16][N:15]([C:20]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[O:21])[CH2:14]1.I[CH3:31]>C(Cl)Cl>[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[CH2:12][C@H:13]1[CH2:18][C@@H:17]([O:19][CH3:31])[CH2:16][N:15]([C:20]([O:22][CH2:23][C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)=[O:21])[CH2:14]1

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 131729315HCID 131729315, compound

Product 1

HCID 131729316HCID 131729316, compoundYield 53.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To cis-phenylmethyl (3RS,5SR)-3-[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)methyl]-5-hydroxy-1-piperidinecarboxylate (380 mg, 0.96 mmol) in 5 mL of CH2Cl2 was added iodomethane (1 mL, 16.1 mmol) and Ag2O (1.15 g, 5.0 mmol). The reaction was allowed to stir at room temperature under nitrogen for 48 h. The reaction mixture was filtered through a pad of Celite® which was washed with 25 mL CH2Cl2, and concentrated under reduced pressure. The crude residue was purified by chromatography on silica gel using a 10-100% EtOAc/hexanes gradient to provide the desired compound (210 mg; 53%) as a colorless oil.

Workup

  1. filtrationThe reaction mixture was filtered through a pad of Celite® which
  2. washwas washed with 25 mL CH2Cl2
  3. concentrationconcentrated under reduced pressure
  4. customThe crude residue was purified by chromatography on silica gel using a 10-100% EtOAc/hexanes gradient

Sources & evidence

ORD record
ord-98311c3773ce497da65875fe8b8e9923
Source dataset
uspto-grants-2011_12
Patent number
US08071592B2

Reaction notes

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