Lithium Hydroxide → N-Boc-N-methylethylenediamine

HRID 2234673Notes

Reaction equation

HRID 2234673 reaction equation
[C:1]([O:5][C:6](=[O:18])[N:7]([CH3:17])[CH2:8][CH2:9][NH:10]C(=O)C(F)(F)F)([CH3:4])([CH3:3])[CH3:2].[OH-].[Li+]>CO>[C:1]([O:5][C:6](=[O:18])[N:7]([CH2:8][CH2:9][NH2:10])[CH3:17])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 10635722Methyl-[2-(2,2,2-trifluoro-acetylamino)-ethyl]-carbamic acid tert-butyl ester

Product 1

HCID 2756424N-Boc-N-methylethylenediamineYield 18%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl-[2-(2,2,2-trifluoro-acetylamino)-ethyl]-carbamic acid tert-butyl ester (1.04 g, 3.85 mmol) in methanol (60 mL) was added 1 M aqueous lithium hydroxide (34 mL, 34.00 mmol). The mixture was stirred at room temperature overnight. It was then concentrated and ethyl acetate (50 mL) was added. The precipitate was filtered off and the filtrate concentrated to give 120 mg (18%) of (2-amino-ethyl)-methyl-carbamic acid tert-butyl ester. 1H-NMR (250 MHz, CDCl3) δ 3.22 (t, J=6.5 Hz, 2H), 2.72-2.86 (m, 5H), 1.36 (s, 9H).

Workup

  1. concentrationIt was then concentrated
  2. additionethyl acetate (50 mL) was added
  3. filtrationThe precipitate was filtered off
  4. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-ce4f9f51668a4670861bb07c2cda3835
Source dataset
uspto-grants-2010_05
Patent number
US07709645B2

Reaction notes

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