tert-Butyl (2-(methoxy(methyl)amino)-2-oxoethyl)carbamate → tert-Butyl (2-oxopropyl)carbamate

HRID 2037734Notes

Reaction equation

HRID 2037734 reaction equation
CON(C)[C:4](=[O:14])[CH2:5][NH:6][C:7](=[O:13])[O:8][C:9]([CH3:12])([CH3:11])[CH3:10].[CH3:16][Mg+].[Br-]>C1COCC1>[O:14]=[C:4]([CH3:16])[CH2:5][NH:6][C:7](=[O:13])[O:8][C:9]([CH3:12])([CH3:11])[CH3:10]

Participants

4

Reactant 2

HCID 4428209tert-Butyl (2-(methoxy(methyl)amino)-2-oxoethyl)carbamateHCID 178418689HCID 178418689, compound

Product 1

HCID 357955tert-Butyl (2-oxopropyl)carbamateYield 72%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl 2-(methoxy(methyl)amino)-2-oxoethylcarbamate (4.36 g, 0.02 mol) in THF (50 mL) added MeMgBr (40 ml, 0.08 ol) at −78° C. The formed mixture was stirred overnight. The mixture was quenched with NH4Cl and extracted with EtOAc. The organic phase was separated, dried over anhydrous Na2SO4, concentrated and purified by column chromatography to give tert-butyl 2-oxopropylcarbamate (2.5 g, 72%). 1H NMR (400 MHz, CDCl3): δ=1.42 (s, 9H), 2.18 (s, 3H), 4.01 (s, 2H), 5.22 (s, 1H).

Workup

  1. customThe mixture was quenched with NH4Cl
  2. extractionextracted with EtOAc
  3. customThe organic phase was separated
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated
  6. custompurified by column chromatography

Sources & evidence

ORD record
ord-ee14afc0a8d647029fc37246ce71ef5f
Source dataset
uspto-grants-2013_11
Patent number
US08575156B2

Reaction notes

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