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

HRID 1824164ノート

反応式

HRID 1824164 の反応式
[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

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 11791229Dichloronickel;hexahydrate触媒HCID 887Methanol溶媒

反応条件

温度
-40 °C

実験手順

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%): 1H NMR (400 MHz, CDCl3) δ 8.43, 7.66, 7.28, 7.15, 4.42, 3.13–3.00, 2.97–2.91, 2.63–2.55, 1.81–1.72.

後処理

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

出典と根拠

ORDレコード
ord-34beb2c54ce94473b957a2e7b9b4151c
出典データセット
uspto-grants-2006_05
特許番号
US07041672B2

反応ノート

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