Sodium borohydride → 6,7-Dihydro-5H-cyclopenta[b]pyridin-5-amine

HRID 1612249노트

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HRID 1612249 반응식
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]2/[C:7](=[N:10]\O)/[CH2:8][CH2:9][C:2]=12.[BH4-].[Na+]>CO.O.O.O.O.O.O.[Ni](Cl)Cl>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]2[CH:7]([NH2:10])[CH2:8][CH2:9][C:2]=12

참가 물질

5

반응물 2

HCID 4311764Sodium borohydrideHCID 45079548(5Z)-N-Hydroxy-6,7-dihydro-5H-cyclopenta[b]pyridin-5-imine

생성물 1

HCID 221473916,7-Dihydro-5H-cyclopenta[b]pyridin-5-amine수율 68%

시약·촉매·용매 2

HCID 11791229Dichloronickel;hexahydrate촉매HCID 887Methanol용매

반응 조건

온도
-40 °C

실험 절차

To a solution of (5Z)-6,7-dihydro-5H-cyclopenta[b]pyridin-5-one oxime (320 mg) in methanol (20 ml) under N2 was added nickel chloride hexahydrate. The reaction mixture was cooled to −40° C. and sodium borohydride (817 mg) was slowly added over 30 min. The reaction mixture was warmed to ambient temperature for 1 h and silica gel was added. The reaction mixture was concentrated. MPLC chromatography was run using a biotage 25S column with 5-8% methanol/methylene chloride with 0.5% ammonium hydroxide to provide the title compound as an oil (197 mg, 68%):

후처리

  1. temperatureThe reaction mixture was warmed to ambient temperature for 1 h
  2. additionsilica gel was added
  3. concentrationThe reaction mixture was concentrated

출처 및 근거

ORD 기록
ord-7ac5142c568a49cab3783507aeb72a8c
출처 데이터셋
uspto-grants-2006_01
특허 번호
US06992087B2

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