2-Phenylquinoline → 2-Phenyl-1,2,3,4-tetrahydroquinoline

HRID 589088

反応式

HRID 589088 の反応式
[C:1]1([C:7]2[CH:16]=[CH:15][C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>C(O)(=O)C.C(OCC)(=O)C>[C:1]1([CH:7]2[CH2:16][CH2:15][C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[NH:8]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

参加物

4

反応物 1

HCID 715452-Phenylquinoline

生成物 1

HCID 107529152-Phenyl-1,2,3,4-tetrahydroquinoline収率 98%

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A solution of 2-phenylquinoline, (0.248 g, 1.21 mmol) [Aldrich, cat. #299650] in acetic acid (6.0 mL) was treated with borane-pyridine complex (0.605 mL, 5.99 mmol) and stirred at room temperature for 18 h. The reaction mixture was diluted with ethyl acetate (50 mL) and washed with 3 M sodium hydroxide solution (70 mL), water (20 mL), and brine (20 mL). The organic layer was dried over sodium sulfate, filtered, and concentrated to give a crude oil. Purification by flash column chromatography (100% hexanes to 25% ethyl acetate/hexanes) gave the desired product (0.247 g, 98%) as a racemic mixture. LCMS calculated for C15H16N (M+H)+: m/z=210.1. found: 210.1.

後処理

  1. washwashed with 3 M sodium hydroxide solution (70 mL), water (20 mL), and brine (20 mL)
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto give a crude oil
  6. customPurification by flash column chromatography (100% hexanes to 25% ethyl acetate/hexanes)

出典と根拠

ORDレコード
ord-c26dcbe135874475b1d1ad6f9a20c542
出典データセット
uspto-grants-2016_01
特許番号
US09227985B2

関連ノート

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