1-{5'-[3,4-Bis(hydroxymethyl)benzylamino]-2,2'-dimethylbiphenyl-4-yl}-1-propanone → (4-{[4'-(1-Ethyl-1-hydroxypropyl)-6,2'-dimethylbiphenyl-3-ylamino]methyl}-2-hydroxymethylphenyl)methanol

HRID 584327Notes

Reaction equation

HRID 584327 reaction equation
[OH:1][CH2:2][C:3]1[CH:4]=[C:5]([CH:26]=[CH:27][C:28]=1[CH2:29][OH:30])[CH2:6][NH:7][C:8]1[CH:9]=[CH:10][C:11]([CH3:25])=[C:12]([C:14]2[CH:19]=[CH:18][C:17]([C:20](=[O:23])[CH2:21][CH3:22])=[CH:16][C:15]=2[CH3:24])[CH:13]=1.[CH2:31]([Mg]Br)[CH3:32]>C1COCC1>[CH2:21]([C:20]([C:17]1[CH:18]=[CH:19][C:14]([C:12]2[C:11]([CH3:25])=[CH:10][CH:9]=[C:8]([NH:7][CH2:6][C:5]3[CH:26]=[CH:27][C:28]([CH2:29][OH:30])=[C:3]([CH2:2][OH:1])[CH:4]=3)[CH:13]=2)=[C:15]([CH3:24])[CH:16]=1)([OH:23])[CH2:31][CH3:32])[CH3:22]

Participants

4

Reactant 2

HCID 223456351-{5'-[3,4-Bis(hydroxymethyl)benzylamino]-2,2'-dimethylbiphenyl-4-yl}-1-propanoneHCID 178418443HCID 178418443, compound

Product 1

HCID 11978013(4-{[4'-(1-Ethyl-1-hydroxypropyl)-6,2'-dimethylbiphenyl-3-ylamino]methyl}-2-hydroxymethylphenyl)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

450 mg (1.1 mmol) of 1-{5′-[3,4-bis(hydroxymethyl)benzylamino]-2,2′-dimethylbiphenyl-4-yl}-1-propanone are dissolved in 30 ml of THF. 1.5 ml (4.5 mmol) of ethylmagnesium bromide are added and the medium is stirred at room temperature for 1 hour. After the usual work-up, the residue is purified by chromatography on silica gel (eluent: 1 heptane/1 ethyl acetate). A white solid is obtained (m=130 mg; Y=27%).

Workup

  1. customAfter the usual work-up, the residue is purified by chromatography on silica gel (eluent: 1 heptane/1 ethyl acetate)
  2. customA white solid is obtained (m=130 mg; Y=27%)

Sources & evidence

ORD record
ord-50ab98f9e0744637aa2e3c3ac2869e72
Source dataset
uspto-grants-2005_08
Patent number
US06924400B2

Reaction notes

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