TBAF tetrahydrofuran → 4-{[(4-Hydroxy-2-methyl-phenyl)-methyl-amino]-methyl}-2-methyl-benzoic Acid Methyl Ester

HRID 424809노트

반응식

HRID 424809 반응식
[CH3:1][O:2][C:3](=[O:29])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][N:11]([C:13]2[CH:18]=[CH:17][C:16]([O:19][Si](C(C)(C)C)(C)C)=[CH:15][C:14]=2[CH3:27])[CH3:12])=[CH:6][C:5]=1[CH3:28].CCCC[N+](CCCC)(CCCC)CCCC.[F-].C1COCC1>C1COCC1>[CH3:1][O:2][C:3](=[O:29])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][N:11]([C:13]2[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][C:14]=2[CH3:27])[CH3:12])=[CH:6][C:5]=1[CH3:28]

참가 물질

4

반응물 2

HCID 11078149TBAF tetrahydrofuranHCID 667041694-({[4-(Tert-butyl-dimethyl-silanyloxy)-2-methyl-phenyl]-methyl-amino}-methyl)-2-methyl-benzoic acid methyl ester

생성물 1

HCID 574433374-{[(4-Hydroxy-2-methyl-phenyl)-methyl-amino]-methyl}-2-methyl-benzoic Acid Methyl Ester수율 71.6%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 4-({[4-(tert-butyl-dimethyl-silanyloxy)-2-methyl-phenyl]-methyl-amino}-methyl)-2-methyl-benzoic acid methyl ester (1.0 g, 2.1 mmol) in THF (20.0 mL) is added 1.0 M TBAF/THF (3.2 mL, 3.2 mmol) at room temperature. The reaction mixture is stirred for 1.0 h. The reaction mixture is partitioned between EtOAc (30 mL) and water (30 mL). The organic phase is washed with brine (30 mL), dried (Na2SO4), filtered, and concentrated under reduced pressure to a residue. The residue is purified by flash chromatography to give the title compound as oil (0.45 g, 62%). LC-ES/MS: 300.3 (M+1), 298.3 (M−1).

후처리

  1. customThe reaction mixture is partitioned between EtOAc (30 mL) and water (30 mL)
  2. washThe organic phase is washed with brine (30 mL)
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure to a residue
  6. customThe residue is purified by flash chromatography

출처 및 근거

ORD 기록
ord-7ce31479ea2f4d0dbfcaf2ece218acd7
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08106077B2

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