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

HRID 605808노트

반응식

HRID 605808 반응식
[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

참가 물질

5

반응물 2

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

생성물 1

HCID 17986993N-BOC-4-(phenylethynyl)piperidine수율 90.9%

시약·촉매·용매 2

HCID 83717Copper iodide촉매HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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))

출처 및 근거

ORD 기록
ord-7594c6b3670548099df7075756b0f7c0
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07915261B2

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