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

HRID 1379370Notes

Reaction equation

HRID 1379370 reaction equation
[CH3:1][NH:2][CH2:3][CH2:4][OH:5].Cl[C:7]([O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:8].C(OCC)(=O)C>C(Cl)Cl>[CH2:10]([O:9][C:7]([N:2]([CH3:1])[CH2:3][CH2:4][OH:5])=[O:8])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 80162-(Methylamino)ethanolHCID 8857Ethyl AcetateHCID 10387Benzyl chloroformate

Product 1

HCID 13279869N-Cbz-N-methyl-2-aminoethanol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To N-methylethanolamine (149 mmol) in methylene chloride (100 ml) at 0° C. was added benzyl chloroformate (70 mmol). The mixture was stirred at 0° C. for 30 min, then at room temperature for 1 h, poured into ethyl acetate, washed with 2M HCl, saturated NaHCO3 solution, and brine, then dried over Na2SO4 and evaporated to provide the desired compound. 1H NMR (CDCl3,TMS) δ 7.36 (m, 5H), 5.14 (s,2H), 3.78 (m, 2H), 3.47 (m, 2H), 3.01 (s, 3H).

Workup

  1. waitat room temperature for 1 h
  2. washwashed with 2M HCl, saturated NaHCO3 solution, and brine
  3. dry with materialdried over Na2SO4
  4. customevaporated

Sources & evidence

ORD record
ord-e1f010894341411ea3676c97127bbd76
Source dataset
uspto-grants-1997_09
Patent number
US05670675

Reaction notes

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