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

HRID 589088

반응식

HRID 589088 반응식
[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

참가 물질

4

반응물 1

HCID 715452-Phenylquinoline

생성물 1

HCID 107529152-Phenyl-1,2,3,4-tetrahydroquinoline수율 98%

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-c26dcbe135874475b1d1ad6f9a20c542
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09227985B2

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