2-(Methylamino)ethanol → N-Cbz-N-methyl-2-aminoethanol

HRID 888062Notes

Reaction equation

HRID 888062 reaction equation
Cl[C:2]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:3].[CH3:12][NH:13][CH2:14][CH2:15][OH:16]>C1COCC1.C(=O)([O-])[O-].[Na+].[Na+]>[CH2:5]([O:4][C:2]([N:13]([CH2:14][CH2:15][OH:16])[CH3:12])=[O:3])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 2

HCID 80162-(Methylamino)ethanolHCID 10387Benzyl chloroformate

Product 1

HCID 13279869N-Cbz-N-methyl-2-aminoethanolYield 97%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 10340Sodium CarbonateSolvent

Conditions

Temperature
0 °C

Procedure

Benzyl chloroformate (19 g, 111.1 mmol) in THF (20 mL) was added dropwise over 15 min to a stirred solution of 2-(methylamino)ethanol (10 g, 133.3 mmol) in THF (100 mL) and aqueous sodium carbonate (100 mL) at 0° C. The reaction mixture was stirred at 0° C. for 12 h and then extracted with EtOAc (2×200 mL). The organic layer was washed with aqueous sodium carbonate (200 mL) and dried (potassium carbonate) and solvent was removed under reduced pressure to give the title compound (22.5 g, 97% yield).

Workup

  1. extractionextracted with EtOAc (2×200 mL)
  2. washThe organic layer was washed with aqueous sodium carbonate (200 mL)
  3. dry with materialdried (potassium carbonate) and solvent
  4. customwas removed under reduced pressure

Sources & evidence

ORD record
ord-134e810bdb4944d2a203443afad4ea7d
Source dataset
uspto-grants-2012_08
Patent number
US08247564B2

Reaction notes

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