Iodobenzene → N-BOC-4-(phenylethynyl)piperidine

HRID 605808ノート

反応式

HRID 605808 の反応式
[C:1]([CH:3]1[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:4]1)#[CH:2].I[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C1COCC1.[Cu](I)I>[C:17]1([C:2]#[C:1][CH:3]2[CH2:4][CH2:5][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:7][CH2:8]2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

参加物

5

反応物 2

HCID 11575IodobenzeneHCID 15550481tert-Butyl 4-ethynylpiperidine-1-carboxylate

生成物 1

HCID 17986993N-BOC-4-(phenylethynyl)piperidine収率 90.9%

試薬・触媒・溶媒 2

HCID 83717Copper iodide触媒HCID 8028Tetrahydrofuran溶媒

実験手順

Tert-butyl 4-ethynylpiperidine-1-carboxylate (12.5 g) and iodobenzene (12.8 g) was dissolved in THF:TEA=1:1 (v/v) mixed solvent (125 ml), then at room temperature, copper iodide (455 mg) and palladium tetrakistriphenylphosphine complex (1.38 g) were added thereto in that order, followed by stirring overnight at room temperature. The solvent was evaporated, EtOAc was added to it, and washed with aqueous 1 M hydrochloric acid solution, water and saturated brine in that order. This was dried over magnesium sulfate, and the solvent was evaporated to obtain a light brown oil. This was purified by silica gel column chromatography (eluent: hexane:EtOAc=19:1 (v/v)) to obtain tert-butyl 4-(phenylethynyl)piperidine-1-carboxylate (15.5 g) as a light brown oil.

後処理

  1. customThe solvent was evaporated
  2. additionEtOAc was added to it
  3. washwashed with aqueous 1 M hydrochloric acid solution, water and saturated brine in that order
  4. dry with materialThis was dried over magnesium sulfate
  5. customthe solvent was evaporated
  6. customto obtain a light brown oil
  7. customThis was purified by silica gel column chromatography (eluent: hexane:EtOAc=19:1 (v/v))

出典と根拠

ORDレコード
ord-7594c6b3670548099df7075756b0f7c0
出典データセット
uspto-grants-2011_03
特許番号
US07915261B2

反応ノート

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