Methyl iodide → 1,1-Dimethylethyl N-cyclopropyl-N-[[6-(3-methoxypropyl)-8-quinolinyl]methyl]carbamate

HRID 337579Notes

Reaction equation

HRID 337579 reaction equation
[CH:1]1([N:4]([CH2:12][C:13]2[CH:14]=[C:15]([CH2:23][CH2:24][CH2:25][OH:26])[CH:16]=[C:17]3[C:22]=2[N:21]=[CH:20][CH:19]=[CH:18]3)[C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8])[CH2:3][CH2:2]1.[H-].[Na+].I[CH3:30]>C1COCC1>[CH:1]1([N:4]([CH2:12][C:13]2[CH:14]=[C:15]([CH2:23][CH2:24][CH2:25][O:26][CH3:30])[CH:16]=[C:17]3[C:22]=2[N:21]=[CH:20][CH:19]=[CH:18]3)[C:5](=[O:11])[O:6][C:7]([CH3:9])([CH3:10])[CH3:8])[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 66895821HCID 66895821, compound

Product 1

HCID 668965621,1-Dimethylethyl N-cyclopropyl-N-[[6-(3-methoxypropyl)-8-quinolinyl]methyl]carbamate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1,1-dimethylethyl cyclopropyl{[6-(3-hydroxypropyl)-8-quinolinyl]methyl}carbamate (1 eq.) from the previous step in THF (0.3 M) was added sodium hydride (60% (w/w) dispersion in paraffin oil, 1.2 eq.). The resulting suspension was stirred at RT for 15 min before iodomethane (1.4 eq.) was added. The now yellow solution was stirred at RT for 12 h before the reaction was quenched with the addition of 1 N aq. NaOH. The aqueous layer was separated and back-extracted with ether. The combined organic extracts were washed further with water and brine, dried over Na2SO4, filtered and the filtrate concentrated in vacuo. Purification of the crude product thus obtained by way of flash chromatography (SiO2, 9:1 (v/v) Hex:EtOAc→EtOAc) afforded the title compound as a colorless oil.

Workup

  1. additionwas added
  2. customwas quenched with the addition of 1 N aq. NaOH
  3. customThe aqueous layer was separated
  4. extractionback-extracted with ether
  5. washThe combined organic extracts were washed further with water and brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationthe filtrate concentrated in vacuo
  9. customPurification of the crude product
  10. customthus obtained by way of flash chromatography (SiO2, 9:1 (v/v) Hex:EtOAc→EtOAc)

Sources & evidence

ORD record
ord-b1697f09717644bab60ad8fe82cca778
Source dataset
uspto-grants-2014_11
Patent number
US08889714B2

Reaction notes

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