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

HRID 2117473

反応式

HRID 2117473 の反応式
[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

参加物

9

反応物 5

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 887Methanol溶媒HCID 8857Ethyl Acetate溶媒HCID 14798Sodium Hydroxide溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-322d350f90c741c5a4382e5e5843009f
出典データセット
uspto-grants-2008_10
特許番号
US07442702B2

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