Sodium Cyanide → 1-(Diphenylmethyl)azetidine-3-carbonitrile

HRID 865026ノート

反応式

HRID 865026 の反応式
[CH:1]([N:14]1[CH2:17][CH:16](OS(C)(=O)=O)[CH2:15]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C-:23]#[N:24].[Na+]>CN(C)C=O.O>[CH:1]([N:14]1[CH2:17][CH:16]([C:23]#[N:24])[CH2:15]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

5

反応物 2

HCID 8929Sodium CyanideHCID 27587161-(Diphenylmethyl)azetidin-3-yl methanesulfonate

生成物 1

HCID 27792901-(Diphenylmethyl)azetidine-3-carbonitrile収率 51.3%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
60 °C

実験手順

A mixture of 50 g (0.157 mol) of 1-benzhydryl-3-mesyloxyazetidine (J. Org. Chem. 1972, 37, 3953-3955) and 23.5 g (0.479 mol) of sodium cyanide in 340 ml of dimethylformamide and 43 ml of water is heated to 60° C. for 5 hours. The reaction mixture is left at ambient temperature overnight and is then poured into 2000 ml of water/ice. The solid product is recovered by filtration and is purified by being suspended in 800 ml of water and being filtered. The product thus obtained is dried and crystallized from isopropyl ether to obtain 20 g of 1-benzhydryl-3-azetidinecarbonitrile. M.p. 142°-146° C.

後処理

  1. filtrationThe solid product is recovered by filtration
  2. customis purified
  3. filtrationbeing filtered
  4. customThe product thus obtained
  5. customis dried
  6. customcrystallized from isopropyl ether

出典と根拠

ORDレコード
ord-2993db46b6ac4e8e91a517121cc8ed03
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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