Tetrabutylammonium Fluoride → HCID 54089467, 화합물

HRID 1740615노트

반응식

HRID 1740615 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:20]=[CH:19][C:18]([CH2:21][O:22][Si](C(C)(C)C)(C)C)=[C:17]([O:30][C:31]([F:34])([F:33])[F:32])[CH:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([O:14][C:15]2[CH:20]=[CH:19][C:18]([CH2:21][OH:22])=[C:17]([O:30][C:31]([F:34])([F:32])[F:33])[CH:16]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

참가 물질

4

반응물 2

HCID 2724141Tetrabutylammonium FluorideHCID 18700148HCID 18700148, 화합물

생성물 1

HCID 54089467HCID 54089467, 화합물

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

To a stirred solution of 4-(N-tert-butyloxy-carbonyl-4-piperidinyloxy)-1-(tert-butyldimethylsilyloxymethyl)-2-trifluoromethoxybenzene (3.5 g, 7.1 mmol) from Step 5 above in THF (50 mL) was added TBAF (8 mL of a 1.0 M solution in THF, 8 mmol). The mixture was stirred at ambient temperature for 5 minutes and the solvent was removed under reduced pressure. The residue was partitioned between EtOAc (100 mL) and water (2×50 mL). The organic phase was dried (MgSO4), filtered, and the solvent was removed under reduced pressure. The residue was purified by pressurized silica gel column chromatography using a gradient elution of 25-50% EtOac:hexanes to give 4-(N-tert-butyloxycarbonyl-4-piperidinyloxy)-2-(trifluoromethoxy)benzyl alcohol as a colorless gum (TLC Rf =0.24 (25% EtOAc EtOAc:hexanes)).

후처리

  1. customthe solvent was removed under reduced pressure
  2. customThe residue was partitioned between EtOAc (100 mL) and water (2×50 mL)
  3. dry with materialThe organic phase was dried (MgSO4)
  4. filtrationfiltered
  5. customthe solvent was removed under reduced pressure
  6. customThe residue was purified by pressurized silica gel column chromatography
  7. washa gradient elution of 25-50% EtOac

출처 및 근거

ORD 기록
ord-895eded7dd9645d98ee3394d0420c428
출처 데이터셋
uspto-grants-1999_10
특허 번호
US05968938

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