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

HRID 865029ノート

反応式

HRID 865029 の反応式
[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

参加物

9

反応物 5

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

生成物 1

HCID 100840771-Benzhydryl-3-methylazetidine-3-carbonitrile収率 91.5%

試薬・触媒・溶媒 3

HCID 313Hydrochloric Acid触媒HCID 8028Tetrahydrofuran溶媒3 回HCID 8058Hexane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-fddc7c5c058a4797a8316b5ab1f4cb58
出典データセット
uspto-grants-1996_10
特許番号
US05565474

反応ノート

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