Water → 3-(2,4-Dimethoxybenzyl)-4-oxo-3-azabicyclo[3.1.0]hexane-1-carbaldehyde

HRID 83577

Reaction equation

HRID 83577 reaction equation
[CH3:1][O:2][C:3]1[CH:18]=[C:17]([O:19][CH3:20])[CH:16]=[CH:15][C:4]=1[CH2:5][N:6]1[CH2:11][C:10]2([CH2:12][OH:13])[CH:8]([CH2:9]2)[C:7]1=[O:14].C(N(CC)CC)C.O>CCCCCC.C(OCC)(=O)C>[CH3:1][O:2][C:3]1[CH:18]=[C:17]([O:19][CH3:20])[CH:16]=[CH:15][C:4]=1[CH2:5][N:6]1[C:7](=[O:14])[CH:8]2[C:10]([CH:12]=[O:13])([CH2:9]2)[CH2:11]1

Participants

5

Reactant 3

HCID 962WaterHCID 8471TriethylamineHCID 712879123-(2,4-Dimethoxybenzyl)-5-hydroxymethyl-3-azabicyclo[3.1.0]hexan-2-one

Product 1

HCID 866803893-(2,4-Dimethoxybenzyl)-4-oxo-3-azabicyclo[3.1.0]hexane-1-carbaldehydeYield 118.3%

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

Under argon atmosphere, to a solution of 3-(2,4-dimethoxybenzyl)-5-hydroxymethyl-3-azabicyclo[3.1.0]hexan-2-one (9.2 mg) in dimethylsulfoxide/chloroform (2/1, 135 μl) were sequentially added triethylamine (23 μl) and sulfur trioxide-pyridine complex (10.6 mg) at room temperature, and the mixture was stirred for 2 hours. To this reaction mixture was added water, and the mixture was extracted with ethyl acetate. This organic layer was washed with water, a saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure to give a crude product of the titled compound (10.8 mg).

Workup

  1. customat room temperature
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThis organic layer was washed with water
  4. dry with materiala saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9ad52f814abf4597bd635ad8910ca526
Source dataset
uspto-grants-2014_09
Patent number
US08846746B2

Linked notes

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