Methyl iodide → 1,1-Dimethylethyl N-(3-methoxypropyl)-N-methylcarbamate

HRID 1669195Notes

Reaction equation

HRID 1669195 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][CH2:5][NH:6][C:7](=[O:13])[O:8][C:9]([CH3:12])([CH3:11])[CH3:10].[OH-].[K+].[CH3:16]I>>[CH3:1][O:2][CH2:3][CH2:4][CH2:5][N:6]([CH3:16])[C:7](=[O:13])[O:8][C:9]([CH3:10])([CH3:12])[CH3:11]

Participants

4

Reactant 3

HCID 6328Methyl iodideHCID 14797Potassium HydroxideHCID 11389877HCID 11389877, compound

Product 1

HCID 574476911,1-Dimethylethyl N-(3-methoxypropyl)-N-methylcarbamateYield 37%

Conditions

Temperature
20 °C

Procedure

A suspension of carbamate 270 (5.0 g, 26.4 mmol), crushed KOH (3.8 g, 67.7 mmol) in MeI (15 mL) was stirred at 20° C. for 72 h under N2. The solution was filtered through Celite, washed with DCM (2×50 mL) and the solvent evaporated. The residue was purified by chromatography, eluting with a gradient (30-50%) of EtOAc/pet. ether, to give carbamate 271 (2.0 g, 37%) as a colourless oil: 1H NMR δ 3.38 (t, J=6.3 Hz, 2H, CH2N), 3.33 (s, 3H, OCH3), 3.28 (t, J=7.0 Hz, 2H, CH2O), 2.85 (s, 3H, NCH3), 1.78 (tt, J=7.0, 6.3 Hz, 2H, CH2), 1.46 [s, 9H, C(CH3)3]; MS (APCI) m/z 104 (MH+-tBuCO2, 100%); HRMS (FAB+) calcd for C10H22NO3 (MH+) m/z 204.1600, found 204.1605.

Workup

  1. filtrationThe solution was filtered through Celite
  2. washwashed with DCM (2×50 mL)
  3. customthe solvent evaporated
  4. customThe residue was purified by chromatography
  5. washeluting with a gradient (30-50%) of EtOAc/pet. ether

Sources & evidence

ORD record
ord-2e3ae6ba4c9a47579f72c10a57cbf03a
Source dataset
uspto-grants-2011_08
Patent number
US07989451B2

Reaction notes

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