Tetrabutylammonium Fluoride → HCID 54089467、化合物

HRID 2289356ノート

反応式

HRID 2289356 の反応式
[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]

参加物

4

反応物 2

HCID 2724141Tetrabutylammonium FluorideHCID 18700148HCID 18700148、化合物

生成物 1

HCID 54089467HCID 54089467、化合物

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

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)).

後処理

  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

出典と根拠

ORDレコード
ord-d4b3240ef8d04f34b875ee1213b67e81
出典データセット
uspto-grants-2000_07
特許番号
US06090805

反応ノート

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