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

HRID 1018474노트

반응식

HRID 1018474 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

반응 조건

온도
4 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-6c5fad7f5fbe475c8a4f306fa135e6b7
출처 데이터셋
uspto-grants-2002_11
특허 번호
US06482824B1

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