Sodium hydride → HCID 58696357, compound

HRID 1178347Notes

Reaction equation

HRID 1178347 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C@@:9]([NH:15][CH3:16])([CH2:12][CH:13]=[CH2:14])[CH2:10][OH:11])[CH:5]=[CH:6][C:7]=1[Cl:8].[H-].[Na+].[CH3:19][O:20][C:21]1[CH:22]=[C:23]([CH:26]=[C:27]([O:31][CH3:32])[C:28]=1[O:29][CH3:30])[CH2:24]Cl>CN(C)C=O>[CH3:32][O:31][C:27]1[CH:26]=[C:23]([CH:22]=[C:21]([O:20][CH3:19])[C:28]=1[O:29][CH3:30])[CH2:24][O:11][CH2:10][C@:9]([C:4]1[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=1)([NH:15][CH3:16])[CH2:12][CH:13]=[CH2:14]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 774485-(Chloromethyl)-1,2,3-trimethoxybenzeneHCID 58696371HCID 58696371, compound

Product 1

HCID 58696357HCID 58696357, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

Under argon, a solution of 2-(S)-(3,4-dichlorophenyl)-2-methylamino-4-penten-1-ol (8.5 g) in anhydrous N,N-dimethylformamide (50 mL) was added to a suspension of sodium hydride (1.5 g) in anhydrous N,N-dimethylformamide (50 mL) under cooling with ice, and the mixture was stirred for 1 hour at room temperature. A solution of 3,4,5-trimethoxybenzyl chloride (7.8 g) in anhydrous N,N-dimethylformamide (30 mL) was added to the reaction mixture under cooling with ice, and the resultant mixture was stirred overnight at room temperature. The reaction mixture was poured into ice-water, extracted with ether, sequentially washed with water and saturated brine, and dried over sodium sulfate anhydrate. The solvent was concentrated under reduced pressure, and the residue was purified through silica gel column chromatography (n-hexane:ethyl acetate=5:1 to 2:1→ethyl acetate), to thereby give the title compound (11.8 g, 81.8%).

Workup

  1. temperatureunder cooling with ice
  2. temperatureunder cooling with ice
  3. extractionextracted with ether
  4. washsequentially washed with water and saturated brine
  5. dry with materialdried over sodium sulfate anhydrate
  6. concentrationThe solvent was concentrated under reduced pressure
  7. customthe residue was purified through silica gel column chromatography (n-hexane:ethyl acetate=5:1 to 2:1→ethyl acetate)

Sources & evidence

ORD record
ord-c00410923ba9489fb92619b01807427c
Source dataset
uspto-grants-2007_10
Patent number
US07276511B2

Reaction notes

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