Methyl iodide → HCID 59400094, compound

HRID 2389540Notes

Reaction equation

HRID 2389540 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6]([CH:26]=[CH:27][C:28]=1[Cl:29])[CH2:7][N:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH2:11][CH:10]([NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])[CH2:9]1.I[CH3:31]>O1CCCC1>[Cl:3][C:4]1[CH:5]=[C:6]([CH:26]=[CH:27][C:28]=1[Cl:29])[CH2:7][N:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH2:11][CH:10]([N:18]([CH3:31])[C:19](=[O:25])[O:20][C:21]([CH3:23])([CH3:24])[CH3:22])[CH2:9]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 59400204HCID 59400204, compound

Product 1

HCID 59400094HCID 59400094, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydride (0.1 g, 4.16 mmol) was added to a 0° C. solution of tert-butyl 1-(3,4-dichlorobenzyl)-1,2,3,4-tetrahydroquinolin-3-ylcarbamate (0.85 g, 2.09 mmol) and iodomethane (95%, 2.97, 10 eq) in anhydrous tetrahydrofuran (10 mL). The mixture was stirred at room temperature for 1 hour. The mixture was quenched by slowly adding few drops of water. The resulting mixture was dried over anhydrous sodium sulfate and the solvent evaporated. The residue was purified by flash chromatography (eluted with 5% EtOAc in hexane) to give tert-butyl 1-(3,4-dichlorobenzyl)-1,2,3,4-tetrahydroquinolin-3-yl(methyl)carbamate as white solid (789 mg). 1H NMR (DMSO) 400 MHz δ 7.57 (d, J=4 Hz, 1H), 7.61 (brd, J=6.4 Hz, 1H), 7.47 (d, J=1.6, 1H), 7.23 (dd, J=2.0 Hz and 8.4 Hz, 1H), 6.95 (d, J=7.6 Hz, 1H), 6.91 (m, 1H), 6.53 (m, 1H), 6.45 (d, 8.4 Hz, 1H), 4.45 (brd, J=10.4 Hz, 1H), 4.29 (br, 1H), 3.40 (t, 10.4 Hz, 1H), 3.21 (m, 1H), 3.02 (m, 1H), 2.74 (m, 1H), 2.72 (s, 3H), 1.36 (m, 9H). LCMS m/e 422 (M+H).

Workup

  1. customThe mixture was quenched
  2. additionby slowly adding few drops of water
  3. dry with materialThe resulting mixture was dried over anhydrous sodium sulfate
  4. customthe solvent evaporated
  5. customThe residue was purified by flash chromatography (eluted with 5% EtOAc in hexane)

Sources & evidence

ORD record
ord-2b7b445f5a42443caaf815d6efdeb6da
Source dataset
uspto-grants-2012_09
Patent number
US08273754B2

Reaction notes

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