Bromoacetonitrile → Ethyl 1-benzyl-4-(cyanomethyl)-3-oxopiperidine-4-carboxylate

HRID 1501838ノート

反応式

HRID 1501838 の反応式
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:10](=[O:19])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[Si]([N-][Si](C)(C)C)(C)C.[K+].Br[CH2:31][C:32]#[N:33]>O1CCCC1>[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([CH2:31][C:32]#[N:33])([C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:10](=[O:19])[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

5

反応物 3

HCID 11534BromoacetonitrileHCID 419705Ethyl 3-oxo-1-(phenylmethyl)-4-piperidinecarboxylateHCID 3251421Potassium bis(trimethylsilyl)amide

生成物 1

HCID 86709485Ethyl 1-benzyl-4-(cyanomethyl)-3-oxopiperidine-4-carboxylate

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
0 °C

実験手順

Into a 250-mL 3-necked round-bottom flask was placed a solution of ethyl 1-benzyl-3-oxopiperidine-4-carboxylate (10 g, 38.27 mmol, 1.00 equiv) in tetrahydrofuran (80 mL). This was followed by the addition of a solution of KHMDS in tetrahydrofuran (42 mL, 1M) dropwise with stirring at 0° C., and 30 min later, 2-bromoacetonitrile (6.89 g, 57.44 mmol, 1.50 equiv) was added dropwise with stirring at 0° C. The resulting solution was stirred for 4 h at room temperature. The resulting mixture was concentrated under vacuum. The residue was applied onto a silica gel column and eluted with ethyl acetate/petroleum ether to give the title compound.

後処理

  1. customInto a 250-mL 3-necked round-bottom flask was placed
  2. stirringwith stirring at 0° C
  3. stirringThe resulting solution was stirred for 4 h at room temperature
  4. concentrationThe resulting mixture was concentrated under vacuum
  5. washeluted with ethyl acetate/petroleum ether

出典と根拠

ORDレコード
ord-a9ba9fd918bb4f6ca535c782bee52992
出典データセット
uspto-grants-2015_12
特許番号
US09206198B2

反応ノート

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