1-Phenylcyclobutanecarbonitrile → (1-Phenylcyclobutyl)methanamine

HRID 1057406노트

반응식

HRID 1057406 반응식
[C:1]1([C:7]2([C:11]#[N:12])[CH2:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[C:1]1([C:7]2([CH2:11][NH2:12])[CH2:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

참가 물질

4

반응물 2

HCID 844001-PhenylcyclobutanecarbonitrileHCID 21226445Aluminium lithium hydride

생성물 1

HCID 15611176(1-Phenylcyclobutyl)methanamine수율 53%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

To a solution of 1-phenylcyclobutanecarbonitrile (0.96 g, 6.09 mmol) in anhydrous tetrahydrofuran (40 mL) was added a 1 N solution of lithium aluminum hydride (LAH) in tetrahydrofuran (12 mL, 12 mmol). After stirring 2 h at ambient temperature, the excess LAH was slowly quenched with water (10 mL) and diluted with additional tetrahydrofuran (20 mL). This was then reacted with 0.25 N aqueous NaOH (5 mL) at ambient temperature for 20 h and filtered, the filtrate concentrated in vacuo, and the residue purified by flash coliumn chromatography (10% methanol in dichloromethane, saturated with ammonia gas) giving the title compound as a yellow oil (0.52 g, 53%). 1H NMR (300 MHz, CDCl3) δ 7.32 (m, 2H), 7.19 (m, 1H), 7.10 (m, 2H), 2.93 (s, 2H), 2.38-2.26 (m, 2H), 2.18-2.01 (m, 3H), 1.92-1.82 (m, 1H), 1.14 (bs, 2H).

후처리

  1. customthe excess LAH was slowly quenched with water (10 mL)
  2. additiondiluted with additional tetrahydrofuran (20 mL)
  3. customThis was then reacted with 0.25 N aqueous NaOH (5 mL) at ambient temperature for 20 h
  4. filtrationfiltered
  5. concentrationthe filtrate concentrated in vacuo
  6. customthe residue purified by flash coliumn chromatography (10% methanol in dichloromethane, saturated with ammonia gas)

출처 및 근거

ORD 기록
ord-cf03d174a8934673a1b995c66ca5ae50
출처 데이터셋
uspto-grants-2003_02
특허 번호
US06514978B2

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