Chlorotrimethylsilane → 2-(2-Cyclopropyl-6-(trifluoromethyl)pyridin-3-yl)ethanamine

HRID 1626525노트

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HRID 1626525 반응식
[BH4-].[Li+].Cl[Si](C)(C)C.[CH:8]1([C:11]2[C:16](/[CH:17]=[CH:18]/[N+:19]([O-])=O)=[CH:15][CH:14]=[C:13]([C:22]([F:25])([F:24])[F:23])[N:12]=2)[CH2:10][CH2:9]1>C1COCC1>[CH:8]1([C:11]2[C:16]([CH2:17][CH2:18][NH2:19])=[CH:15][CH:14]=[C:13]([C:22]([F:25])([F:23])[F:24])[N:12]=2)[CH2:10][CH2:9]1

참가 물질

5

반응물 3

HCID 6397ChlorotrimethylsilaneHCID 4148881Lithium borohydrideHCID 67287702(E)-2-cyclopropyl-3-(2-nitrovinyl)-6-(trifluoromethyl)pyridine

생성물 1

HCID 672872742-(2-Cyclopropyl-6-(trifluoromethyl)pyridin-3-yl)ethanamine수율 97.4%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

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온도
0 °C

실험 절차

To a stirred solution of lithium borohydride (232 μL, 0.465 mmol) in THF was added chlorotrimethylsilane (118 μL, 0.930 mmol) dropwise. After stirring for 15 minutes, argon was bubbled through the reaction mixture for 2 minutes to eliminate any trimethylsilane in the reaction mixture. (E)-2-cyclopropyl-3-(2-nitrovinyl)-6-(trifluoromethyl)pyridine (30 mg, 0.116 mmol) was added (in 1 mL of THF). The reaction was heated to reflux for 2 hours, cooled to 0° C. and carefully quenched with methanol (1 mL). The reaction mixture was concentrated, diluted with dichloromethane and 20% aqueous KOH. The layers were separated and the organic layer was dried over sodium sulfate, filtered and concentrated to yield 2-(2-cyclopropyl-6-(trifluoromethyl)pyridin-3-yl)ethanamine (26 mg, 0.113 mmol, 97.2% yield).

후처리

  1. customargon was bubbled through the reaction mixture for 2 minutes
  2. temperatureThe reaction was heated
  3. temperatureto reflux for 2 hours
  4. customcarefully quenched with methanol (1 mL)
  5. concentrationThe reaction mixture was concentrated
  6. additiondiluted with dichloromethane and 20% aqueous KOH
  7. customThe layers were separated
  8. dry with materialthe organic layer was dried over sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated

출처 및 근거

ORD 기록
ord-a019586482ca4869a98e2a54617693c8
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08785445B2

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