Water → Racemic-(trans)-1-benzhydryl-3-methoxy-2-methylazetidine

HRID 80846Notes

Reaction equation

HRID 80846 reaction equation
[CH:1]([N:14]1[CH2:17][C@@H:16]([OH:18])[C@@H:15]1[CH3:19])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.I[CH3:21].[H-].[Na+].O>C1COCC1>[CH:1]([N:14]1[CH2:17][C@@H:16]([O:18][CH3:21])[C@@H:15]1[CH3:19])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 10243988(2s,3r)-1-(Diphenylmethyl)-2-methylazetidin-3-ol

Product 1

HCID 71244838Racemic-(trans)-1-benzhydryl-3-methoxy-2-methylazetidine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of racemic-(trans)-1-benzhydryl-2-methylazetidin-3-ol (0.198 g, 0.782 mmol) in THF (16 mL) was added iodomethane (98 μL, 1.6 mmol) and sodium hydride (0.035 g, 0.86 mmol, 60% in mineral oil). After 1.5 h, water was added and the mixture was extracted with EtOAc (3×). The combined organic phases were washed with brine, dried with sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified via FCC (0-15% EtOAc/n-heptanes) to give the title compound. MS (ESI+) m/z 268.2 (M+H)+.

Workup

  1. extractionthe mixture was extracted with EtOAc (3×)
  2. washThe combined organic phases were washed with brine
  3. dry with materialdried with sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified via FCC (0-15% EtOAc/n-heptanes)

Sources & evidence

ORD record
ord-b8755da1588c4b88ac56b1cc08608857
Source dataset
uspto-grants-2014_09
Patent number
US08846656B2

Reaction notes

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