Tetrabutylammonium Fluoride → Tert-butyl 4-(4-ethynylphenyl)piperidine-1-carboxylate

HRID 1487941노트

반응식

HRID 1487941 반응식
C[Si]([C:5]#[C:6][C:7]1[CH:12]=[CH:11][C:10]([CH:13]2[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]2)=[CH:9][CH:8]=1)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1.O>[C:6]([C:7]1[CH:8]=[CH:9][C:10]([CH:13]2[CH2:14][CH2:15][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:17][CH2:18]2)=[CH:11][CH:12]=1)#[CH:5]

참가 물질

5

반응물 2

HCID 2724141Tetrabutylammonium FluorideHCID 59805220Tert-butyl 4-(4-((trimethylsilyl)ethynyl)phenyl)piperidine-1-carboxylate2회

생성물 1

HCID 59805226Tert-butyl 4-(4-ethynylphenyl)piperidine-1-carboxylate수율 93.4%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

Into a 50-mL round-bottom flask, was placed a solution of tert-butyl 4-(4-((trimethylsilyl)ethynyl)phenyl)piperidine-1-carboxylate (compound 76.2, 1.34 g, 3.75 mmol) in tetrahydrofuran (20 mL). Tetrabutylammonium fluoride (1.95 g, 7.47 mmol) was added and the resulting solution was stirred for 10 min at room temperature. The mixture was diluted with water (30 mL) and extracted with EtOAc (3×20 mL). The organic layers were combined, dried (Na2SO4), filtered and concentrated under reduced pressure to yield the title compound as a brown oil (1.0 g, crude).

후처리

  1. customInto a 50-mL round-bottom flask, was placed
  2. extractionextracted with EtOAc (3×20 mL)
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-cdaf1e369a05411ab19041d75c229d44
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09428502B2

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