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

HRID 2409989ノート

反応式

HRID 2409989 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-9a1e83f0f3b84ab2bd0f1e8a9a121be8
出典データセット
uspto-grants-2014_08
特許番号
US08815903B2

反応ノート

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