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Ethanolamine → (9H-fluoren-9-yl)methyl N-(2-hydroxyethyl)carbamate

HRID 2238349
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HRID 2238349 반응식
[CH2:1]([CH2:3][NH2:4])[OH:2].C(=O)(O)[O-].[Na+].[CH:10]1[C:22]2[CH:21]([CH2:23][O:24][C:25](Cl)=[O:26])[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:14]=2[CH:13]=[CH:12][CH:11]=1>O1CCCC1.O>[CH:10]1[C:22]2[CH:21]([CH2:23][O:24][C:25](=[O:26])[NH:4][CH2:3][CH2:1][OH:2])[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:14]=2[CH:13]=[CH:12][CH:11]=1
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참가 물질

6

반응물 3

HCID 700EthanolamineHCID 343679-Fluorenylmethyl chloroformateHCID 516892Sodium Bicarbonate

생성물 1

HCID 2817739(9H-fluoren-9-yl)methyl N-(2-hydroxyethyl)carbamate수율 52.9%

시약·촉매·용매 2

HCID 962Water용매2회HCID 8028Tetrahydrofuran
용매
2회

실험 절차

To a stirred mixture of ethanolamine (0.49 g, 8 mmol), tetrahydrofuran, water and sodium bicarbonate (1.5 g, 18 mmol) at 6° C., was added a solution 9-fluorenylmethylchloroformate (2.27 g, 8.8 mmol) in tetrahydrofuran in one portion, stirring was continued for 1 h allowing the mixture to warm to room temperature. The mixture was diluted with water and extracted with ethyl acetate. The combined organic extracts were dried over anhydrous magnesium sulfate filtered and evaporated to a crude product. The crude product was re-crystallised from dichloromethane to give (2-hydroxy-ethyl)-carbamic acid 9H-fluoren-9-ylmethyl ester as a white solid (1.2 g).

후처리

  1. extractionextracted with ethyl acetate
  2. dry with materialThe combined organic extracts were dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. customevaporated to a crude product
  5. customThe crude product was re-crystallised from dichloromethane

출처 및 근거

ORD 기록
ord-2437c5aa6f314b68a318f378916906c8
출처 데이터셋
uspto-grants-2010_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07718767B2

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