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

HRID 1038041노트

반응식

HRID 1038041 반응식
I[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:8]([O:12][C:13]([N:15]1[CH2:20][CH2:19][CH:18]([C:21]#[CH:22])[CH2:17][CH2:16]1)=[O:14])([CH3:11])([CH3:10])[CH3:9].C(N(CC)CC)C>C(#N)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I>[C:8]([O:12][C:13]([N:15]1[CH2:20][CH2:19][CH:18]([C:21]#[C:22][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:17][CH2:16]1)=[O:14])([CH3:11])([CH3:10])[CH3:9]

참가 물질

7

반응물 3

HCID 8471TriethylamineHCID 11575IodobenzeneHCID 15550481tert-Butyl 4-ethynylpiperidine-1-carboxylate

생성물 1

HCID 17986993N-BOC-4-(phenylethynyl)piperidine수율 25.9%

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 178418476HCID 178418476, 화합물촉매HCID 6342Acetonitrile용매

실험 절차

Iodobenzene (135 μl, 1.2 mmols), 4-ethynyl-piperidine-1-carboxylic acid tert-butyl ester (209 mg, 1 mmols) and triethylamine (167 μl, 1.2 mmols) were dissolved in acetonitrile (6 ml). Dichlorobis(triphenylphosphine)palladium(II) (35 mg, 0.05 mmols) and CuI (10 mg, 0.05 mmols) were added, and reaction mixture was stirred at room temperature overnight and continued to stir at 50 C for two more hours before partitioning between ethyl acetate and water. Organic layer was isolated, washed with 1 N HCl, brine and dried (MgSO4). Solvents were removed and residue was purified by column chromatography on silica gel using solutions of ethyl acetate in hexanes (1:4; 1:2) to yield the title compound (74 mg). LCMS m/e (230, M-t-Bu+2H)

후처리

  1. customreaction mixture
  2. stirringto stir at 50 C for two more hours
  3. custombefore partitioning between ethyl acetate and water
  4. customOrganic layer was isolated
  5. washwashed with 1 N HCl, brine
  6. dry with materialdried (MgSO4)
  7. customSolvents were removed
  8. customresidue was purified by column chromatography on silica gel using solutions of ethyl acetate in hexanes (1:4; 1:2)

출처 및 근거

ORD 기록
ord-f246f9ddbbbb4452b0ccd6bcdbc0f627
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08546404B2

반응 노트

불러오는 중…