Methyl Ethyl Ketone → HCID 22175789, compound

HRID 1927794Notes

Reaction equation

HRID 1927794 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:7])[CH2:5][NH2:6].[CH2:8](N(CC)CC)C.C[C:16](=O)[CH2:17][CH3:18].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CO.CC(O)=O>[CH3:2][O:3][C:4](=[O:7])[CH2:5][NH:6][CH2:8][CH:17]([CH3:16])[CH3:18]

Participants

6

Reactant 4

HCID 6569Methyl Ethyl KetoneHCID 8471TriethylamineHCID 122755Glycine methyl ester hydrochlorideHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 22175789HCID 22175789, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 10129899Acetic acid methanolSolvent

Procedure

Glycine methylester hydrochloride (2.0 g, 16.0 mmol) was dissolved in MeOH/AcOH (9:1, 25 ml). Triethylamine (1.8 g, 18.0 mmol) was added followed by 2-butanone (1.3 g, 18.0 mmol). After 2 h at room temperature sodium triacetoxyborohydride (3.81 g, 18.0 mmol) was added. After 18 h at room temperature the solvent was removed in vacuo and the residue was taken up in chloroform (200 ml). This solution was washed with sat. NaHCO3, water and brine, dried (Na2SO4) and evaporated in vacuo to give a colourless oil identified as the title compound (646 mg, 4.46 mmol, 28%).

Workup

  1. customAfter 18 h at room temperature the solvent was removed in vacuo
  2. washThis solution was washed with sat. NaHCO3, water and brine
  3. dry with materialdried (Na2SO4)
  4. customevaporated in vacuo
  5. customto give a colourless oil

Sources & evidence

ORD record
ord-10ce34f5c72e442d9885738f2168034e
Source dataset
uspto-grants-2012_05
Patent number
US08183280B2

Reaction notes

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