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

HRID 2117473노트

반응식

HRID 2117473 반응식
[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

참가 물질

9

반응물 5

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

생성물 1

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

시약·촉매·용매 3

HCID 887Methanol용매HCID 8857Ethyl Acetate용매HCID 14798Sodium Hydroxide용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-322d350f90c741c5a4382e5e5843009f
출처 데이터셋
uspto-grants-2008_10
특허 번호
US07442702B2

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