Methyl iodide → HCID 71112708, compound

HRID 1775504Notes

Reaction equation

HRID 1775504 reaction equation
[OH:1][C@@H:2]1[C@@H:7]2[CH2:8][C@@H:4]([C:5](=[O:18])[N:6]2[CH2:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)[CH2:3]1.[H-].[Na+].[CH3:21]I>C1COCC1>[CH3:21][O:1][C@@H:2]1[C@@H:7]2[CH2:8][C@@H:4]([C:5](=[O:18])[N:6]2[CH2:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)[CH2:3]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 51022394HCID 51022394, compound

Product 1

HCID 71112708HCID 71112708, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of the (1S,4R,6S)-6-hydroxy-2-(4-methoxybenzyl)-2-azabicyclo[2.2.1]-heptan-3-one (500 mg, 2.02 mmol) in anhydrous THF (20 mL) was added NaH (60 wt %, 4.04 mmol) at room temperature. The mixture was stirred at 40° C. for 30 min. After cooling to room temperature, CH3I (0.41 mL, 8.08 mmol) was added. The reaction mixture was stirred for 1 h at ambient temperature and quenched with water (50 mL), extracted by EtOAc. The combined organic extracts were washed with brine, dried over Na2SO4, and evaporated to give (1S,4R,6S)-6-methoxy-2-(4-methoxybenzyl)-2-azabicyclo[2.2.1]heptan-3-one. MS (ESI+): m/z 262 (M+H+).

Workup

  1. temperatureAfter cooling to room temperature
  2. stirringThe reaction mixture was stirred for 1 h at ambient temperature
  3. customquenched with water (50 mL)
  4. extractionextracted by EtOAc
  5. washThe combined organic extracts were washed with brine
  6. dry with materialdried over Na2SO4
  7. customevaporated

Sources & evidence

ORD record
ord-642c4b8774a748088c6187b5c7e4ff55
Source dataset
uspto-grants-2016_02
Patent number
US09260452B2

Reaction notes

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