Acetic Acid → {[4-(tert-Butyl-dimethyl-silanyloxy)-2-methyl-phenyl]-methyl-amino}-methyl-2-methyl-benzoic Acid Methyl Ester

HRID 424807Notes

Reaction equation

HRID 424807 reaction equation
[C:1]([Si:5]([CH3:17])([CH3:16])[O:6][C:7]1[CH:12]=[CH:11][C:10]([NH:13][CH3:14])=[C:9]([CH3:15])[CH:8]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:18][O:19][C:20](=[O:30])[C:21]1[CH:26]=[CH:25][C:24](C=O)=[CH:23][C:22]=1[CH3:29].[C:31](O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[CH3:18][O:19][C:20](=[O:30])[C:21]1[CH:26]=[CH:25][C:14]([N:13]([C:10]2[CH:11]=[CH:12][C:7]([O:6][Si:5]([C:1]([CH3:4])([CH3:3])[CH3:2])([CH3:17])[CH3:16])=[CH:8][C:9]=2[CH3:15])[CH3:31])=[C:23]([CH3:24])[C:22]=1[CH3:29]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 5049666Sodium triacetoxyborohydrideHCID 20134203Methyl 4-formyl-2-methylbenzoateHCID 667041204-[(tert-butyldimethylsilyl)oxy]-N,2-dimethylaniline

Product 1

HCID 86629252{[4-(tert-Butyl-dimethyl-silanyloxy)-2-methyl-phenyl]-methyl-amino}-methyl-2-methyl-benzoic Acid Methyl EsterYield 115.1%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of [4-(tert-butyl-dimethyl-silanyloxy)-2-methyl-phenyl]-methyl-amine (0.64 g, 2.6 mmol) and 4-formyl-2-methyl-benzoic acid methyl ester (0.38 g, 2.1 mmol), acetic acid (0.25 g, 4.2 mmol) in 1,2-dichloroethane (10.0 mL) is added sodium triacetoxyborohydride (0.89 g, 4.2 mmol) in portions. The mixture is stirred at room temperature overnight. The reaction is quenched with 5% aq. sodium bicarbonate (5 mL) and is partitioned between EtOAc (60 mL) and water (50 mL). The organic layer is washed with brine (50 mL), dried (Na2SO4), filtered, and concentrated. The residue is purified by flash column chromatography to afford the title compound as a syrup (1.0 g, 95%). LC-ES/MS m/e 414.3 (M+1).

Workup

  1. customThe reaction is quenched with 5% aq. sodium bicarbonate (5 mL)
  2. customis partitioned between EtOAc (60 mL) and water (50 mL)
  3. washThe organic layer is washed with brine (50 mL)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue is purified by flash column chromatography

Sources & evidence

ORD record
ord-ff6204d4d15f4ce89216d214b76f467c
Source dataset
uspto-grants-2012_01
Patent number
US08106077B2

Reaction notes

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