Trifluoroacetic acid → ethyl 1-Cyanomethyliso-nipecotate

HRID 2194127ノート

反応式

HRID 2194127 の反応式
[CH2:1]([O:3][C:4]([C:6]1([CH2:19][C:20]#[N:21])[CH2:11][CH2:10][N:9](C(OC(C)(C)C)=O)[CH2:8][CH2:7]1)=[O:5])[CH3:2].FC(F)(F)C(O)=O>C(Cl)Cl>[CH2:1]([O:3][C:4]([C:6]1([CH2:19][C:20]#[N:21])[CH2:7][CH2:8][NH:9][CH2:10][CH2:11]1)=[O:5])[CH3:2]

参加物

4

反応物 2

HCID 6422Trifluoroacetic acidHCID 533020741-tert-Butyl 4-ethyl 4-(cyanomethyl)piperidine-1,4-dicarboxylate

生成物 1

HCID 59577916ethyl 1-Cyanomethyliso-nipecotate

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

4-Cyanomethyl-piperidine-1,4-dicarboxylic acid 1-tert-butyl ester 4-ethyl ester (36 g) was dissolved in methylene chloride (600 ml), cooled to 0° C. then trifluoroacetic acid (207.8 g, 134.9 ml) was added under an argon atmosphere and the mixture was stirred over night allowing the temperature of the reaction mixture to rise to RT. The reaction mixture was then concentrated in vacuo, the residue taken up in methylene chloride and washed several times with 1M aqueous NaOH (to pH 12). The layers were separated, the organic layer washed with brine, dried over sodium sulphate and concentrated to give 4-cyanomethyl-piperidine-4-carboxylic acid ethyl ester a brown oil (14.2 g) which was essentially pure according to NMR and used in next reaction step without further purification. MS (ESI): 197.2 (MH+).

後処理

  1. customto rise to RT
  2. concentrationThe reaction mixture was then concentrated in vacuo
  3. washwashed several times with 1M aqueous NaOH (to pH 12)
  4. customThe layers were separated
  5. washthe organic layer washed with brine
  6. dry with materialdried over sodium sulphate
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-2eaf1f89899f43118834db5b92f9f68a
出典データセット
uspto-grants-2012_12
特許番号
US08329904B2

反応ノート

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