Sodium cyanoborohydride → 3-Phenyl-2-furanmethanamine

HRID 915689

反応式

HRID 915689 の反応式
[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

参加物

4

反応物 2

HCID 5003444Sodium cyanoborohydrideHCID 134657043-Phenylfuran-2-carbaldehyde

生成物 1

HCID 691299233-Phenyl-2-furanmethanamine収率 13.1%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-04b5727dfaa54c1e9c06cb272af8238e
出典データセット
uspto-grants-2007_09
特許番号
US07265246B2

関連ノート

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