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llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
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tert-butyl N-hydroxycarbamate → (1S,4S)-1-(2-Benzyloxy-ethyl)-2-oxa-3-aza-bicyclo[2.2.2]oct-5-ene-3-carboxylic acid tert-butyl ester

HRID 1804765
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인쇄 미리보기

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HRID 1804765 반응식
[C:1]1([CH2:7][CH2:8][O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:6][CH2:5][CH:4]=[CH:3][CH:2]=1.[C:17]([NH:24][OH:25])([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18].CCC[N+](CCC)(CCC)CCC.[O-]I(=O)(=O)=O>C(Cl)Cl>[C:20]([O:19][C:17]([N:24]1[C@H:4]2[CH2:5][CH2:6][C@:1]([CH2:7][CH2:8][O:9][CH2:10][C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=3)([CH:2]=[CH:3]2)[O:25]1)=[O:18])([CH3:23])([CH3:22])[CH3:21]
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참가 물질

5

반응물 3

HCID 97534tert-butyl N-hydroxycarbamateHCID 3020483Tetrapropylammonium periodateHCID 59152681(2-Cyclohexa-1,3-dienyl-ethoxymethyl)-benzene

생성물 1

HCID 59152652(1S,4S)-1-(2-Benzyloxy-ethyl)-2-oxa-3-aza-bicyclo[2.2.2]oct-5-ene-3-carboxylic acid tert-butyl ester

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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온도
0 °C

실험 절차

(2-Cyclohexa-1,3-dienyl-ethoxymethyl)-benzene (9) (6 g, 28 mmol) is dissolved in 280 ml of dry methylene chloride and cooled down to 0° C. After addition of molecular sieves (6 g, UOP Type 4A) and N—BOC-hydroxylamine (5.6 g, 42 mmol) in small portions, tetrapropylammonium(meta)periodate (10.8 g, 28 mmol) is added slowly in small portions the mixture was stirred for 1 h. Then the mixture is diluted with CH2C12 and cooled to −10° C. 2M Na2S2O5 solution is added slowly (exothermic!). The mixture is washed with water, dried over Na2SO4 and evaporated under reduced pressure. The crude product is purified by Flash-chromatography (ethyl acetate/hexanes (1:9), silicagel).

후처리

  1. additionis added slowly in small portions the mixture
  2. additionThen the mixture is diluted with CH2C12
  3. temperaturecooled to −10° C
  4. washThe mixture is washed with water
  5. dry with materialdried over Na2SO4
  6. customevaporated under reduced pressure
  7. customThe crude product is purified by Flash-chromatography (ethyl acetate/hexanes (1:9), silicagel)

출처 및 근거

ORD 기록
ord-621291e8218b44668cf1c76f3611be0d
출처 데이터셋
uspto-grants-2013_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08354431B2

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