Sodium cyanoborohydride → 3-Phenyl-2-furanmethanamine

HRID 915689

반응식

HRID 915689 반응식
[C:1]1([C:7]2[CH:11]=[CH:10][O:9][C:8]=2[CH:12]=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[BH3-]C#[N:16].[Na+]>CO>[C:1]1([C:7]2[CH:11]=[CH:10][O:9][C:8]=2[CH2:12][NH2:16])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

참가 물질

4

반응물 2

HCID 5003444Sodium cyanoborohydrideHCID 134657043-Phenylfuran-2-carbaldehyde

생성물 1

HCID 691299233-Phenyl-2-furanmethanamine수율 13.1%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

Stir a solution of 3-phenylfuran-2-carbaldehyde (401 mg, 2.33 mmol) and NH4OAc (1.79 g, 23.30 mmol) in methanol (8 mL) at room temperature under nitrogen. Add NaCNBH3 (102 mg, 1.63 mmol). After stirring at room temperature for 24 hours, concentrate the mixture, dilute with water (2 mL), basify with 1N sodium hydroxide, and extract with diethyl ether (4×10 mL). Dry the combined organic phases (magnesium sulfate), filter and concentrate. Perform flash chromatography on silica gel eluting with 9:1 ethyl acetate/MeOH to afford 37 mg of the title compound as a yellow solid. 1H NMR (CDCl3) δ 7.19-7.41 (m, 6H), 6.49 (d, J=2 Hz, 1H), 3.95(s, 2H), 1.80 (br s, 2H).

후처리

  1. concentrationconcentrate the mixture
  2. additiondilute with water (2 mL), basify with 1N sodium hydroxide
  3. extractionextract with diethyl ether (4×10 mL)
  4. dry with materialDry the combined organic phases (magnesium sulfate)
  5. filtrationfilter
  6. concentrationconcentrate

출처 및 근거

ORD 기록
ord-04b5727dfaa54c1e9c06cb272af8238e
출처 데이터셋
uspto-grants-2007_09
특허 번호
US07265246B2

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