Potassium Cyanide → Tert-butyl 4-(cyanomethyl)-4-methylpiperidine-1-carboxylate

HRID 1986179ノート

反応式

HRID 1986179 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([CH2:15]OS(C)(=O)=O)([CH3:14])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C-:21]#[N:22].[K+]>CS(C)=O.CCOC(C)=O.O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([CH2:15][C:21]#[N:22])([CH3:14])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

参加物

6

反応物 2

HCID 9032Potassium CyanideHCID 222480521-(Tert-butoxycarbonyl)-4-methyl-4-(methanesulfonyloxymethyl)piperidine

生成物 1

HCID 66660780Tert-butyl 4-(cyanomethyl)-4-methylpiperidine-1-carboxylate収率 77.2%

試薬・触媒・溶媒 3

HCID 679Dimethyl Sulfoxide溶媒HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
130 °C

実験手順

To 4-methanesulfonyloxymethyl-4-methylpiperidine-1-carboxylic acid tert-butyl ester (0.440 g, 1.43 mmol) dissolved in DMSO (3 mL) is added potassium cyanide (0.373 g, 5.73 mmol). The mixture is heated to 130° C. for 18 hours. The reaction mixture is cooled and diluted with EtOAc and water. The organic layer is concentrated, taken up in MeOH and concentrated again to give the title compound as a brown oil (263 mg, 77% yield).

後処理

  1. temperatureThe reaction mixture is cooled
  2. concentrationThe organic layer is concentrated
  3. concentrationconcentrated again

出典と根拠

ORDレコード
ord-846fb18cc1b44195a6abb937a7a8122b
出典データセット
uspto-grants-2009_06
特許番号
US07547691B2

反応ノート

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