Triacetoxyperiodinane → [5-Methoxy-2-(2-oxo-butyl)-phenyl]-carbamic acid t-butyl Ester

HRID 1825158ノート

反応式

HRID 1825158 の反応式
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[C:23]([O:27][C:28](=[O:43])[NH:29][C:30]1[CH:35]=[C:34]([O:36][CH3:37])[CH:33]=[CH:32][C:31]=1[CH2:38][CH:39]([OH:42])[CH2:40][CH3:41])([CH3:26])([CH3:25])[CH3:24]>C1COCC1>[C:23]([O:27][C:28](=[O:43])[NH:29][C:30]1[CH:35]=[C:34]([O:36][CH3:37])[CH:33]=[CH:32][C:31]=1[CH2:38][C:39](=[O:42])[CH2:40][CH3:41])([CH3:25])([CH3:24])[CH3:26]

参加物

4

反応物 2

HCID 159087TriacetoxyperiodinaneHCID 20767944[2-(2-Hydroxy-butyl)-5-methoxy-phenyl]-carbamic acid t-butyl Ester

生成物 1

HCID 20767945[5-Methoxy-2-(2-oxo-butyl)-phenyl]-carbamic acid t-butyl Ester収率 84%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a solution of Dess-Martin reagent (2.82 g, 6.68 mmole) in 80 ml THF cooled at 0° C. was added [2-(2-hydroxy-butyl)-5-methoxy-phenyl]-carbamic acid t-butyl ester 73a (1.64 g, 5.57 mmole) in 20 ml THF. The reaction mixture was stirred and warmed to room temperature for 2 h, quenched with half saturated NaHCO3, extracted with EtOAc. The organic layer was dried over MgSO4 and concentrated. The residue was purified by flash column chromatography (10–15% EtOAc in hexane) to give colorless oil (1.36 g, 84%). 1H NMR (CDCl3) δ 7.67 (1H, bs), 7.48 (1H, s), 6.99–7.03 (1H, m), 6.56–6.60 (1H, m), 3.79 (3H, s), 3.59 (2H, s), 2.53–2.61 (2H, q, J=7.2 Hz), 1.51 (9H, s), 1.02 (3H, t, J=7.2 Hz). ESIMS (MNa+): 316.10.

後処理

  1. customquenched with half saturated NaHCO3
  2. extractionextracted with EtOAc
  3. dry with materialThe organic layer was dried over MgSO4
  4. concentrationconcentrated
  5. customThe residue was purified by flash column chromatography (10–15% EtOAc in hexane)

出典と根拠

ORDレコード
ord-506079f8626541f9b3bbb4645bf8b029
出典データセット
uspto-grants-2006_05
特許番号
US07045528B2

反応ノート

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