2-Methoxyethylamine → HCID 22708215, compound

HRID 353196Notes

Reaction equation

HRID 353196 reaction equation
[CH:1]([C:3]1[CH:8]=[CH:7][C:6]([S:9][C:10]([CH3:19])([CH3:18])[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[CH:5][CH:4]=1)=O.[CH3:20][O:21][CH2:22][CH2:23][NH2:24].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)(O)[O-].[Na+]>ClCCCl.C(OCC)(=O)C>[CH3:20][O:21][CH2:22][CH2:23][NH:24][CH2:1][C:3]1[CH:8]=[CH:7][C:6]([S:9][C:10]([CH3:19])([CH3:18])[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[CH:5][CH:4]=1

Participants

7

Reactant 4

HCID 80182-MethoxyethylamineHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 22708158HCID 22708158, compound

Product 1

HCID 22708215HCID 22708215, compound

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

4.00 g (14.27 mmol) of tert-butyl 2-[(4-formylphenyl)sulphanyl]-2-methylpropanoate (Example II-2) and 1.07 g (14.27 mmol) of 2-methoxyethylamine are dissolved in 80 ml of 1,2-dichloroethane and, after 30 min and after 10 hours, admixed with 4.54 g (21.40 mmol) of sodium triacetoxyborohydride. The reaction is checked by TLC, and ethyl acetate and saturated sodium bicarbonate solution are then added and the product is extracted with ethyl acetate. The organic phase is washed with 1 N HCl and dried over magnesium sulphate, and the product is, after distillative removal of the solvent, purified by silica gel chromatography (ethyl acetate/cyclohexane 1:1).

Workup

  1. additionare then added
  2. extractionthe product is extracted with ethyl acetate
  3. washThe organic phase is washed with 1 N HCl
  4. dry with materialdried over magnesium sulphate
  5. customafter distillative removal of the solvent
  6. custompurified by silica gel chromatography (ethyl acetate/cyclohexane 1:1)

Sources & evidence

ORD record
ord-4e5f3398b6cf45ff810cfcdb0822de94
Source dataset
uspto-grants-2004_06
Patent number
US06750236B2

Reaction notes

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