2-(Methylamino)ethanol → HCID 60740715, compound

HRID 2175985Notes

Reaction equation

HRID 2175985 reaction equation
[CH3:1][NH:2][CH2:3][CH2:4][OH:5].[C:6](=[O:9])([O-])[OH:7].[Na+].[CH2:11]1[CH2:15][O:14]C[CH2:12]1.[CH2:16](C(CC(Cl)=O)C(Cl)=O)[CH3:17]>O>[OH:5][CH2:4][CH2:3][N:2]([CH3:1])[C:15](=[O:14])[CH2:11][CH2:12][C:6]([O:7][CH2:16][CH3:17])=[O:9]

Participants

6

Reactant 4

HCID 80162-(Methylamino)ethanolHCID 8028TetrahydrofuranHCID 516892Sodium BicarbonateHCID 218646082-Ethylbutanedioyl dichloride

Product 1

HCID 60740715HCID 60740715, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 6.2 mL of 2-(methylamino)ethanol, 6.48 g of sodium hydrogen carbonate, 60 mL of THF, and 30 mL of water was added dropwise 10 mL of ethyl succinyl chloride over 30 minutes under ice cooling, followed by stirring for 3 hours. The reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (hexane:ethyl acetate=11:4), thereby obtaining 12.0 g of ethyl 4-[(2-hydroxyethyl)(methyl)amino]-4-oxobutanoate.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was purified by silica gel column chromatography (hexane:ethyl acetate=11:4)

Sources & evidence

ORD record
ord-2479572f9be2402293d32f5f5b7e1b5c
Source dataset
uspto-grants-2015_06
Patent number
US09062032B2

Reaction notes

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