Methanol → HCID 57934190, compound

HRID 1950318Notes

Reaction equation

HRID 1950318 reaction equation
[CH2:1]([N:3]([C:21]1[CH:26]=[C:25]([O:27]C)[CH:24]=[CH:23][C:22]=1[CH:29]1[CH2:38][CH2:37][C:36]2[C:31](=[CH:32][CH:33]=[C:34]([O:39]C)[CH:35]=2)[CH2:30]1)[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([N:11]([CH3:20])[CH2:12][CH2:13][N:14]2[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)=[CH:7][CH:6]=1)[CH3:2].B(Br)(Br)Br.CO.C(=O)(O)[O-].[Na+]>ClCCl>[CH2:1]([N:3]([CH2:4][C:5]1[CH:6]=[CH:7][C:8]([N:11]([CH3:20])[CH2:12][CH2:13][N:14]2[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)=[CH:9][CH:10]=1)[C:21]1[CH:26]=[C:25]([OH:27])[CH:24]=[CH:23][C:22]=1[CH:29]1[CH2:38][CH2:37][C:36]2[CH:35]=[C:34]([OH:39])[CH:33]=[CH:32][C:31]=2[CH2:30]1)[CH3:2]

Participants

6

Reactant 4

HCID 887MethanolHCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 57934092HCID 57934092, compound

Product 1

HCID 57934190HCID 57934190, compoundYield 56.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of ethyl[5-methoxy-2-(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)phenyl]{4-[methyl(2-piperidin-1-ylethyl)amino]benzyl}amine (108 mg) in dichloromethane (5 ml) was added boron tribromide (1.0 M solution in dichloromethane) (1.0 ml) on an ice bath. The solution was stirred for 30 minutes while warming to room temperature, then methanol (2 ml) was added thereto on an ice bath. A saturated aqueous solution of sodium bicarbonate was added thereto, the solution was extracted with ethyl acetate, then washed with brine, dried over anhydrous magnesium sulfate, and then the solvent was evaporated in vacuo. The resulting residue was purified by NH silica gel column chromatography (chloroform-methanol system) to provide the title compound (58 mg).

Workup

  1. extractionthe solution was extracted with ethyl acetate
  2. washwashed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated in vacuo
  5. customThe resulting residue was purified by NH silica gel column chromatography (chloroform-methanol system)

Sources & evidence

ORD record
ord-91b20d2062be4e18a10d53df4a3049b3
Source dataset
uspto-grants-2013_03
Patent number
US08399520B2

Reaction notes

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