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

HRID 1825158노트

반응식

HRID 1825158 반응식
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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-506079f8626541f9b3bbb4645bf8b029
출처 데이터셋
uspto-grants-2006_05
특허 번호
US07045528B2

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