Methyl iodide → Tert-butyl 2-(benzyl(methyl)amino)ethylcarbamate

HRID 576561Notes

Reaction equation

HRID 576561 reaction equation
[CH2:1]([NH:8][CH2:9][CH2:10][NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.I[CH3:20]>C(Cl)(Cl)Cl>[CH2:1]([N:8]([CH2:9][CH2:10][NH:11][C:12](=[O:18])[O:13][C:14]([CH3:15])([CH3:17])[CH3:16])[CH3:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 10634443N-Benzyl-N'-boc-ethylenediamine

Product 1

HCID 50999034Tert-butyl 2-(benzyl(methyl)amino)ethylcarbamateYield 50%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a cooled (˜5° C.) solution of compound A (6.2 g, 25.0 mmol) and TEA (3.0 g, 29.7 mmol, 4.13 mL) in chloroform (50 mL) was added iodomethane (4.2 g, 29.7 mmol, 1.85 mL). The pressure tube was sealed, and the mixture stirred at ambient temperature for 20 h. The mixture was then precipitated with ether (300 mL); the white solid was filtered off and washed with ether (50 mL). The filtrate was concentrated and the residual yellow oil (5.2 g) was purified by silica gel column chromatography (2-10% MeOH gradient in DCM) to give compound B (3.3 g, 12.5 mmol, 50%) as a colorless oil. TLC Rf (DCM/MeOH 9:1): 0.55. LC-MS [M+H] 264.3 (C15H24N2O2+H, calc: 264.4).

Workup

  1. customThe pressure tube was sealed
  2. customThe mixture was then precipitated with ether (300 mL)
  3. filtrationthe white solid was filtered off
  4. washwashed with ether (50 mL)
  5. concentrationThe filtrate was concentrated
  6. customthe residual yellow oil (5.2 g) was purified by silica gel column chromatography (2-10% MeOH gradient in DCM)

Sources & evidence

ORD record
ord-ffc87f0cef0d4569846965a2b2299abf
Source dataset
uspto-grants-2015_05
Patent number
US09040032B2

Reaction notes

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