Methyl 3-formylbenzoate → Methyl 3-{[2-(2-hydroxy-3,3-dimethylbutyl)-4-methoxyphenylamino]methyl}benzoate

HRID 1191654Notes

Reaction equation

HRID 1191654 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[CH2:10][CH:11]([OH:16])[C:12]([CH3:15])([CH3:14])[CH3:13].[CH:17]([C:19]1[CH:20]=[C:21]([CH:26]=[CH:27][CH:28]=1)[C:22]([O:24][CH3:25])=[O:23])=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(O)(=O)C.C(OCC)(=O)C>[OH:16][CH:11]([C:12]([CH3:13])([CH3:15])[CH3:14])[CH2:10][C:3]1[CH:4]=[C:5]([O:8][CH3:9])[CH:6]=[CH:7][C:2]=1[NH:1][CH2:17][C:19]1[CH:20]=[C:21]([CH:26]=[CH:27][CH:28]=1)[C:22]([O:24][CH3:25])=[O:23]

Participants

6

Reactant 3

HCID 639145Methyl 3-formylbenzoateHCID 5049666Sodium triacetoxyborohydrideHCID 69670816HCID 69670816, compound

Product 1

HCID 69670829Methyl 3-{[2-(2-hydroxy-3,3-dimethylbutyl)-4-methoxyphenylamino]methyl}benzoateYield 79.5%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1-(2-amino-5-methoxyphenyl)-3,3-dimethylbutan-2-ol (155 mg) and methyl 3-formylbenzoate (137 mg) in acetic acid (2 mL) was added sodium triacetoxyborohydride (294 mg) at room temperature, and the mixture was stirred for one hour. The reaction mixture was diluted with ethyl acetate and washed with 5% aqueous sodium hydrogen carbonate solution. The organic layer was washed with saturated saline, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane) to obtain the title compound (205 mg).

Workup

  1. washwashed with 5% aqueous sodium hydrogen carbonate solution
  2. washThe organic layer was washed with saturated saline
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane)

Sources & evidence

ORD record
ord-03f10cbda75540aea380bcf7fb252bf9
Source dataset
uspto-grants-2014_03
Patent number
US08680120B2

Reaction notes

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