Hydrochloric Acid → (3-((4-Butyl-benzylamino)-methyl)-phenyl)-acetic acid methyl ester

HRID 2300423Notes

Reaction equation

HRID 2300423 reaction equation
[CH2:1]([C:5]1[CH:12]=[CH:11][C:8]([CH2:9][NH2:10])=[CH:7][CH:6]=1)[CH2:2][CH2:3][CH3:4].Cl.O1CCOCC1.[CH3:20][O:21][C:22](=[O:32])[CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([CH:30]=O)[CH:25]=1.[BH3-]C#N.[Na+]>CO.CCOC(C)=O.[OH-].[Na+]>[CH3:20][O:21][C:22](=[O:32])[CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([CH2:30][NH:10][CH2:9][C:8]2[CH:7]=[CH:6][C:5]([CH2:1][CH2:2][CH2:3][CH3:4])=[CH:12][CH:11]=2)[CH:25]=1

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 40298714-ButylbenzylamineHCID 5003444Sodium cyanoborohydrideHCID 11819590Methyl 2-(3-formylphenyl)acetate

Product 1

HCID 54268705(3-((4-Butyl-benzylamino)-methyl)-phenyl)-acetic acid methyl ester

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of 4-butyl-benzylamine (from Preparation 15, 0.918 g, 6 mmol) in MeOH was added to 4N HCl in dioxane (0.75 mL, 3 mmol) followed by addition of (3-formyl-phenyl)-acetic acid methyl ester (from Preparation 13, 0.534 g, 3.0 mmol). NaCNBH3 (0.194 mL, 3 mmol) was added and the reaction was stirred at room temperature overnight. The mixture was diluted with EtOAc and 2N NaOH was added. The organic solution was dried over MgSO4, filtered, and concentrated in vacuo. The product was purified via flash chromatography (50% hexanes, 50% EtOAc, 0.1% Et3N) to afford the title compound of Step A. 1H NMR (400 MHz, CDCl3) δ 7.08-7.38 (m, 8H), 3.75 (s, 2H), 3.73 (s, 2H), 3.70 (s, 3H), 3.62 (s, 2H), 2.61 (t, 2H), 1.58 (m, 2H), 1.37 (m, 2H), 0.92 (t, 3H); MS 326 (M+1).

Workup

  1. additionwas added
  2. dry with materialThe organic solution was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe product was purified via flash chromatography (50% hexanes, 50% EtOAc, 0.1% Et3N)

Sources & evidence

ORD record
ord-1dd7945544d043a2b0bf29a5dce2c967
Source dataset
uspto-grants-2002_12
Patent number
US06498172B1

Reaction notes

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