Tetrabutylammonium Fluoride → 2'-[(t-Butoxycarbonylamino)methyl]-1,1-biphenyl-4-methanol

HRID 1080744

반응식

HRID 1080744 반응식
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[C:16]1[CH:21]=[CH:20][C:19]([CH2:22][O:23][Si](C(C)(C)C)(C)C)=[CH:18][CH:17]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1.C(OCC)(=O)C>[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[C:16]1[CH:21]=[CH:20][C:19]([CH2:22][OH:23])=[CH:18][CH:17]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

참가 물질

5

반응물 2

HCID 2724141Tetrabutylammonium FluorideHCID 233654482'-[(t-Butoxycarbonylamino)methyl]-4-[(t-butyldimethylsiloxy)-methyl]-1,1'-biphenyl

생성물 1

HCID 220084722'-[(t-Butoxycarbonylamino)methyl]-1,1-biphenyl-4-methanol수율 93%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 8857Ethyl Acetate용매

실험 절차

To a solution of 150 mg (0.35 mmol) of 2'-[(t-butoxycarbonylamino)methyl]-4-[(t-butyldimethylsiloxy)-methyl]-1,1'-biphenyl (Step G) in 2 mL of dry tetrahydrofuran under a nitrogen atmosphere was added by syringe 0.52 mL (0.53 mmol) of 1.0M solution of tetra-n-butylammonium fluoride in tetrahydrofuran. The reaction mixture was stirred for one hour then diluted with 100 mL of ethyl acetate. The mixture was washed with water (3×20 mL), then saturated aqueous sodium chloride, dried over magnesium sulfate and filtered. The solvent was removed under vacuum to give an oil which was purified by column chromatography on silica gel eluting with hexanes/ethyl acetate (55:45) to afford 101 mg (93%) of the product as a white solid. FAB-MS: calculated for C19H23NO3 313; found 314 (M+H). 1H NMR (200 MHz, CDCl3): 1.40 (s, 9H), 2.50 (s, 2H), 4.20 (s, 2H), 4.70 (s, 2H), 7.18-7.45 (s, 8H).

후처리

  1. washThe mixture was washed with water (3×20 mL)
  2. dry with materialsaturated aqueous sodium chloride, dried over magnesium sulfate
  3. filtrationfiltered
  4. customThe solvent was removed under vacuum
  5. customto give an oil which
  6. customwas purified by column chromatography on silica gel eluting with hexanes/ethyl acetate (55:45)

출처 및 근거

ORD 기록
ord-36a9228dd73b4ffbb152b500429a6256
출처 데이터셋
uspto-grants-1996_12
특허 번호
US05583130

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