Methyl iodide → 1-Benzhydryl-3-methylazetidine-3-carbonitrile

HRID 865029노트

반응식

HRID 865029 반응식
[CH:1](NC(C)C)(C)C.[Li]CCCC.[CH:13]([N:26]1[CH2:29][CH:28]([C:30]#[N:31])[CH2:27]1)([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.CI.[NH4+].[Cl-]>O1CCCC1.CCCCCC.Cl>[CH:13]([N:26]1[CH2:29][C:28]([CH3:1])([C:30]#[N:31])[CH2:27]1)([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

참가 물질

9

반응물 5

HCID 6328Methyl iodideHCID 7912DiisopropylamineHCID 25517Ammonium ChlorideHCID 27792901-(Diphenylmethyl)azetidine-3-carbonitrileHCID 178418339Butyllithium

생성물 1

HCID 100840771-Benzhydryl-3-methylazetidine-3-carbonitrile수율 91.5%

시약·촉매·용매 3

HCID 313Hydrochloric Acid촉매HCID 8028Tetrahydrofuran용매3회HCID 8058Hexane용매

실험 절차

A solution of 2.6 g (0.025 mol) of diisopropylamine in 80 ml of anhydrous tetrahydrofuran is cooled to -78° C. under nitrogen and 10 ml of a 2M solution of n-BuLi in n-hexane are added to it with great care. Stirring is carried out for 30 minutes and a solution of 6.2 g (0.025 mol) of 1-benzhydrylazetidine-3-carbonitrile obtained in stage a) of PREPARATION I in 30 ml of tetrahydrofuran is added to it. After 1 hour's stirring, a solution of 7.0 g (0.05 mol) of methyl iodide in 10 ml of tetrahydrofuran is added dropwise. Stirring is carried out for 1 hour and the reaction mixture is allowed to warm up to ambient temperature. It is left to stand overnight and the basic solution is neutralized by addition of approximately 100 ml of a 20% solution of NH4Cl and a few drops of concentrated HCl. The product is extracted with methylene chloride and the organic phase is concentrated to obtain 6.0 g of 1-benzhydryl-3-methyl-3-azetidinecarbonitrile which is crystallized from n-hexane. M.p. 78°-80° C.

후처리

  1. additionis added to it
  2. stirringAfter 1 hour's stirring
  3. stirringStirring
  4. waitis carried out for 1 hour
  5. waitIt is left
  6. waitto stand overnight
  7. extractionThe product is extracted with methylene chloride
  8. concentrationthe organic phase is concentrated

출처 및 근거

ORD 기록
ord-fddc7c5c058a4797a8316b5ab1f4cb58
출처 데이터셋
uspto-grants-1996_10
특허 번호
US05565474

반응 노트

불러오는 중…