Methyl iodide → HCID 118271795, compound

HRID 588126Notes

Reaction equation

HRID 588126 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]1[CH:32]=[CH:31][C:8]([CH2:9][N:10]([CH2:22][C:23]2[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=2)[C@@H:11]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:12]([CH3:15])([OH:14])[CH3:13])=[CH:7][CH:6]=1.[CH3:33]I>C1COCC1>[CH3:33][O:14][C:12]([CH3:15])([CH3:13])[C@H:11]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[N:10]([CH2:9][C:8]1[CH:7]=[CH:6][C:5]([O:4][CH3:3])=[CH:32][CH:31]=1)[CH2:22][C:23]1[CH:24]=[CH:25][C:26]([O:29][CH3:30])=[CH:27][CH:28]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 118272386HCID 118272386, compound

Product 1

HCID 118271795HCID 118271795, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

At 0° C., to a suspension of NaH (0.13 g, 2.96 mmol) in anhydrous THF (5 mL), was added a solution of (S)-1-(bis(4-methoxybenzyl)amino)-2-methyl-1-phenylpropan-2-ol 4 (1.0 g, 2.47 mmol) in anhydrous THF (10 mL). After 15 min, MeI (0.55 g, 3.71 mmol) was added and the contents were heated to reflux. After 8 h, the reaction was brought back to ambient temperature, quenched carefully with ice cold H2O (10 mL), and the organic contents were extracted with EtOAc (3×25 mL). The combined organic extracts were washed with brine (1×20 mL), dried over Na2SO4, concentrated to afford (S)-2-methoxy-N,N-bis(4-methoxybenzyl)-2-methyl-1-phenylpropan-1-amine. H1NMR (CD3OD, 400 MHz) δ 7.45-7.44 (m, 2H), 7.37-7.34 (m, 2H), 7.33-7.28 (m, 5H), 6.88-6.86 (m, 4H), 4.20 (s, 1H), 3.78 (s, 6H), 3.25 (s, 4H), 2.81 (s, 3H), 1.4 (s, 3H), 0.81 (s, 3H). MS: [M+H]+ m/z 420.

Workup

  1. temperaturethe contents were heated to reflux
  2. waitAfter 8 h
  3. customwas brought back to ambient temperature
  4. customquenched carefully with ice cold H2O (10 mL)
  5. extractionthe organic contents were extracted with EtOAc (3×25 mL)
  6. washThe combined organic extracts were washed with brine (1×20 mL)
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-4be2b1a5d75848a79c5e2bdab3373ab3
Source dataset
uspto-grants-2016_01
Patent number
US09226922B2

Reaction notes

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