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

HRID 2117473Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2117473
[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

Komponenten

9

Edukt 5

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 887MethanolLösungsmittelHCID 8857Ethyl AcetateLösungsmittelHCID 14798Sodium HydroxideLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-322d350f90c741c5a4382e5e5843009f
Quelldatensatz
uspto-grants-2008_10
Patentnummer
US07442702B2

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