tert-butyl N-hydroxycarbamate → 2-t-butoxycarbonyl-3,6-dihydro-3,5-dimethyl-6-(4-ethoxyphenyl)-2H-1,2-oxazine

HRID 1018474ノート

反応式

HRID 1018474 の反応式
[OH:1][NH:2][C:3](=[O:9])[O:4][C:5]([CH3:8])([CH3:7])[CH3:6].[CH2:10]([O:12][C:13]1[CH:18]=[CH:17][C:16](/[CH:19]=[C:20](\[CH3:24])/[CH:21]=[CH:22]/[CH3:23])=[CH:15][CH:14]=1)[CH3:11].I([O-])(=O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC>ClCCl>[C:5]([O:4][C:3]([N:2]1[CH:22]([CH3:23])[CH:21]=[C:20]([CH3:24])[CH:19]([C:16]2[CH:15]=[CH:14][C:13]([O:12][CH2:10][CH3:11])=[CH:18][CH:17]=2)[O:1]1)=[O:9])([CH3:8])([CH3:7])[CH3:6]

参加物

5

反応物 3

HCID 97534tert-butyl N-hydroxycarbamateHCID 2724292Tetrabutylammonium PeriodateHCID 184015281-(4-ethoxyphenyl)-2-methylpent-1E,3E-diene

生成物 1

HCID 184015392-t-butoxycarbonyl-3,6-dihydro-3,5-dimethyl-6-(4-ethoxyphenyl)-2H-1,2-oxazine

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

反応条件

温度
4 °C

実験手順

A solution of t-butyl N-hydroxycarbamate (11.14 g, 84 mmol) in dichloromethane (300 ml) was added dropwise over 25 mins to a stirred mixture of 1-(4-ethoxyphenyl)-2-methyl-pent-1E,3E-diene (8.46 g, 42 mmol) and tetrabutylammonium periodate (32.6 g, 75 mmol) in dichloromethane (300 ml) cooled to 4° C. under nitrogen atmosphere. After stirring for 4 h at 3-4° C. the reaction mixture was washed with 2M aqueous sodium carbonate containing sodium metabisulphite and then twice with water. The dichloromethane solution was dried over magnesium sulphate, filtered and evaporated to an oil (33.1 g). This was purified by chromatography twice on silica eluting with n-hexane: diethyl ether 4:1 to give 2-t-butoxycarbonyl-3,6-dihydro-3,5-dimethyl-6-(4-ethoxyphenyl)-2H-1,2-oxazine as a yellow oil.

後処理

  1. washwas washed with 2M aqueous sodium carbonate
  2. additioncontaining sodium metabisulphite
  3. dry with materialThe dichloromethane solution was dried over magnesium sulphate
  4. filtrationfiltered
  5. customevaporated to an oil (33.1 g)
  6. customThis was purified by chromatography twice on silica eluting with n-hexane: diethyl ether 4:1

出典と根拠

ORDレコード
ord-6c5fad7f5fbe475c8a4f306fa135e6b7
出典データセット
uspto-grants-2002_11
特許番号
US06482824B1

反応ノート

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