Methyl iodide → HCID 67090497, compound

HRID 18093Notes

Reaction equation

HRID 18093 reaction equation
[C:1]([O:5][C:6](=[O:29])[NH:7][CH2:8][C@@H:9]1[CH2:14][CH2:13][CH2:12][CH2:11][N:10]1[C:15]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[C:23]1[O:27][N:26]=[C:25]([CH3:28])[N:24]=1)=[O:16])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[H][H].I[CH3:35]>O1CCCC1>[CH3:2][C:1]([O:5][C:6](=[O:29])[N:7]([CH3:35])[CH2:8][C@@H:9]1[CH2:14][CH2:13][CH2:12][CH2:11][N:10]1[C:15]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[C:23]1[O:27][N:26]=[C:25]([CH3:28])[N:24]=1)=[O:16])([CH3:4])[CH3:3]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 86593675((S)-1-{1-[2-(3-Methyl-[1,2,4]-oxadiazol-5-yl)-phenyl]-methanoyl}-piperidin-2-ylmethyl)-carbamic acid tert butyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 67090497HCID 67090497, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

((S)-1-{1-[2-(3-Methyl-[1,2,4]oxadiazol-5-yl)-phenyl]-methanoyl}-piperidin-2-ylmethyl)-carbamic acid tert butyl ester (0.4 g) in tetrahydrofuran (5 ml) was treated with sodium hydride (0.1 g). After evolution of hydrogen had ceased iodomethane (0.1 ml) was added and the reaction stirred for 16 hours. The reaction was quenched with ice/water, extracted with diethyl ether (×3), the combined organic extracts dried and solvent removed at reduced pressure. The residue was column chromatographed (silica gel, diethyl ether) to give the title compound (0.2 g).

Workup

  1. additionwas added
  2. customThe reaction was quenched with ice/water
  3. extractionextracted with diethyl ether (×3)
  4. customthe combined organic extracts dried
  5. customsolvent removed at reduced pressure
  6. customchromatographed (silica gel, diethyl ether)

Sources & evidence

ORD record
ord-21db68bf7f5b4ef199ce0b06e43670f6
Source dataset
uspto-grants-2010_06
Patent number
US07741329B2

Reaction notes

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