2-(3,5-Dimethoxyphenyl)-2-methylpropanal → {2-[2-(3,5-Dimethoxy-phenyl)-2-methyl-propylamino]-4-hydroxy-5-methoxy-phenyl}-(4-isopropyl-phenyl)-methanone

HRID 641860Notes

Reaction equation

HRID 641860 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([OH:8])[C:5]([O:9][CH3:10])=[CH:4][C:3]=1[C:11]([C:13]1[CH:18]=[CH:17][C:16]([CH:19]([CH3:21])[CH3:20])=[CH:15][CH:14]=1)=[O:12].[CH3:22][O:23][C:24]1[CH:25]=[C:26]([C:32]([CH3:36])([CH3:35])[CH:33]=O)[CH:27]=[C:28]([O:30][CH3:31])[CH:29]=1.[BH3-]C#N.[Na+]>C(Cl)Cl>[CH3:31][O:30][C:28]1[CH:27]=[C:26]([C:32]([CH3:36])([CH3:35])[CH2:33][NH:1][C:2]2[CH:7]=[C:6]([OH:8])[C:5]([O:9][CH3:10])=[CH:4][C:3]=2[C:11]([C:13]2[CH:18]=[CH:17][C:16]([CH:19]([CH3:21])[CH3:20])=[CH:15][CH:14]=2)=[O:12])[CH:25]=[C:24]([O:23][CH3:22])[CH:29]=1

Participants

5

Reactant 3

HCID 6017362-(3,5-Dimethoxyphenyl)-2-methylpropanalHCID 5003444Sodium cyanoborohydrideHCID 59259050(2-Amino-4-hydroxy-5-methoxy-phenyl)-(4-isopropyl-phenyl)-methanone

Product 1

HCID 59259033{2-[2-(3,5-Dimethoxy-phenyl)-2-methyl-propylamino]-4-hydroxy-5-methoxy-phenyl}-(4-isopropyl-phenyl)-methanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 41.1 mg (144 μmol) (2-amino-4-hydroxy-5-methoxy-phenyl)-(4-isopropyl-phenyl)-methanone, 45 mg (216 mmol) 2-(3,5-dimethoxy-phenyl)-2-methyl-propionaldehyde, 180 mg molecular sieves (pore size 4 Å) and 0.50 ml CH2Cl2 is stirred for 90 min before 8.23 μl (144 μmol) and 22 mg NaCNBH3 are added. After 16 h the excess of reducing agent is destroyed by addition of 1 M hydrochloric acid and the mixture is basified with 1 M sodium hydroxide solution. The product is extracted with CH2Cl2 and purified by reversed phase preparative HPLC.

Workup

  1. additionare added
  2. customagent is destroyed by addition of 1 M hydrochloric acid
  3. extractionThe product is extracted with CH2Cl2
  4. custompurified by reversed phase preparative HPLC

Sources & evidence

ORD record
ord-b3a392540ba043199171186c2407f8cb
Source dataset
uspto-grants-2010_04
Patent number
US07696216B2

Reaction notes

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