Aluminium lithium hydride → 5-Bromo-2-(piperidin-1-ylmethyl)pyridine

HRID 2366837노트

반응식

HRID 2366837 반응식
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Br:7][C:8]1[CH:9]=[CH:10][C:11]([C:14]([N:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)=O)=[N:12][CH:13]=1>C1COCC1>[Br:7][C:8]1[CH:9]=[CH:10][C:11]([CH2:14][N:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)=[N:12][CH:13]=1

참가 물질

4

반응물 2

HCID 21226445Aluminium lithium hydride2회HCID 263701125-Bromo-2-(piperidin-1-ylcarbonyl)pyridine

생성물 1

HCID 234384095-Bromo-2-(piperidin-1-ylmethyl)pyridine

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

Lithium aluminium hydride in 1M THF (1.858 mL, 1.858 mmol) was cooled to 0° C. 5-bromo-2-(1-piperidinylcarbonyl)pyridine (for a preparation see Intermediate 25) (250 mg, 0.929 mmol) was dissolved in THF (7 mL) and added dropwise to the LiAlH4 under nitrogen and stirred. After addition to the reductant, the solution was warmed to room temperature. After 1 hour the reactions were filtered, washed with EtOAc (3×10 mL) and evaporated to dryness to give a brown/yellow solid (159 mg). This was purified on a 25+S Biotage silica column, eluting with DCM:2M MeOH/NH3 (1:0 to 97:3). Product-containing fractions were evaporated to dryness to give a dark yellow solid (61 mg).

후처리

  1. additionAfter addition to the reductant
  2. filtrationAfter 1 hour the reactions were filtered
  3. washwashed with EtOAc (3×10 mL)
  4. customevaporated to dryness

출처 및 근거

ORD 기록
ord-2c7a188f54f34ef7bf21db5df7ca42a4
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08697725B2

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