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

HRID 1080744

反応式

HRID 1080744 の反応式
[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]

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 8857Ethyl Acetate溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-36a9228dd73b4ffbb152b500429a6256
出典データセット
uspto-grants-1996_12
特許番号
US05583130

関連ノート

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