Triacetoxyperiodinane → Tert-butyl (5-methoxy-2-(3-methyl-2-oxobutyl)phenyl)carbamate

HRID 2409989노트

반응식

HRID 2409989 반응식
[OH:1][CH:2]([CH:20]([CH3:22])[CH3:21])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][C:5]=1[NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>ClCCl>[CH3:11][O:10][C:7]1[CH:8]=[CH:9][C:4]([CH2:3][C:2](=[O:1])[CH:20]([CH3:21])[CH3:22])=[C:5]([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[CH:6]=1

참가 물질

4

반응물 2

HCID 159087TriacetoxyperiodinaneHCID 86703306tert-Butyl [2-(2-hydroxy-3-methylbutyl)-5-methoxyphenyl]carbamate

생성물 1

HCID 69096724Tert-butyl (5-methoxy-2-(3-methyl-2-oxobutyl)phenyl)carbamate수율 94.6%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of tert-butyl [2-(2-hydroxy-3-methylbutyl)-5-methoxyphenyl]-carbamate (100 mg) in dichloromethane (1.5 mL) was added Dess-Martin periodinane (164 mg), and the mixture was stirred at room temperature for 2 hours. The reaction mixture was filtrated through Celite (registered trademark), and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane) to obtain the title compound (94 mg). 1H-NMR (CDCl3) δ ppm: 1.13 (6H, d, J=7.0 Hz), 1.52 (9H, s), 2.72-2.86 (1H, m), 3.66 (2H, s), 3.80 (3H, s), 6.59 (1H, dd, J=2.6, 8.5 Hz), 7.02 (1H, d, J=8.5 Hz), 7.47 (1H, br s), 7.60-7.90 (1H, br).

후처리

  1. filtrationThe reaction mixture was filtrated through Celite (registered trademark)
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane)

출처 및 근거

ORD 기록
ord-9a1e83f0f3b84ab2bd0f1e8a9a121be8
출처 데이터셋
uspto-grants-2014_08
특허 번호
US08815903B2

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