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

HRID 2118248Notes

Reaction equation

HRID 2118248 reaction equation
[CH3:1][NH:2][CH2:3][CH2:4][OH:5].CCN(CC)CC.[CH2:13]([O:20][C:21](Cl)=[O:22])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C(Cl)Cl>[CH2:13]([O:20][C:21](=[O:22])[N:2]([CH2:3][CH2:4][OH:5])[CH3:1])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 80162-(Methylamino)ethanolHCID 8471TriethylamineHCID 10387Benzyl chloroformate

Product 1

HCID 13279869N-Cbz-N-methyl-2-aminoethanolYield 75.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 20.0 g (266.3 mmol) of 2-(methylamino)ethanol was dissolved in 100 mL of CH2Cl2 and treated first with 74.23 mL (532.54 mmol, 2 eq) of Et3N then with 33.8 mL (239.64 mmol, 0.9 eq) of benzylchloroformate within a period of 1.5 h at RT. The reaction was partitioned between Et2O (×3)/aqueous 10% KHSO4 (×2), dried over Na2SO4 and evaporated to yield 37.93 g (68%) of (2-hydroxy-ethyl)-methyl-carbamic acid benzyl ester, MS: 210 (MH+).

Workup

  1. customThe reaction was partitioned between Et2O (×3)/aqueous 10% KHSO4 (×2)
  2. dry with materialdried over Na2SO4
  3. customevaporated

Sources & evidence

ORD record
ord-910b2946169a47f5bdbb844282bc48cd
Source dataset
uspto-grants-2008_10
Patent number
US07442791B2

Reaction notes

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