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Methanol → Tert-butyl ((6-(hydroxymethyl)-1,2,3,4-tetrahydronaphthalen-2-YL)methyl)carbamate

HRID 352838
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HRID 352838 반응식
[C:1]([O:5][C:6]([NH:8][CH2:9][CH:10]1[CH2:19][CH2:18][C:17]2[C:12](=[CH:13][CH:14]=[C:15]([C:20](OC)=[O:21])[CH:16]=2)[CH2:11]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CCCCCC.CO>ClCCl>[C:1]([O:5][C:6]([NH:8][CH2:9][CH:10]1[CH2:19][CH2:18][C:17]2[C:12](=[CH:13][CH:14]=[C:15]([CH2:20][OH:21])[CH:16]=2)[CH2:11]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]
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참가 물질

5

반응물 3

HCID 887MethanolHCID 8058HexaneHCID 22709912Methyl 6-(((tert-butoxycarbonyl)amino)methyl)-5,6,7,8-tetrahydronaphthalene-2-carboxylate

생성물 1

HCID 22709613Tert-butyl ((6-(hydroxymethyl)-1,2,3,4-tetrahydronaphthalen-2-YL)methyl)carbamate수율 72.3%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

In dichloromethane (10 ml), the (2RS)-2-(N-tert-butoxycarbonylaminomethyl)-6-methoxycarbonyl-1,2,3,4-tetrahydronaphthalene (0.47 g) was dissolved. Aluminum diisobutylhydride (a 0.95M hexane solution, 3.60 ml) was added dropwise to the resulting solution at an external temperature of −78° C., followed by stirring for 90 minutes without changing the temperature. Methanol was added to the reaction mixture and the mixture was heated to room temperature. The insoluble matter was filtered off from filtration through Celite. The filtrate was concentrated under reduced pressure. The concentrate was diluted with dichloromethane, washed with water and dried over anhydrous sodium sulfate. The residue obtained by distilling off the solvent under reduced pressure was purified by chromatography on a silica gel column (hexane:ethyl acetate 3:1), whereby colorless crystals (0.31 g, 72%) was obtained. A portion of the resulting crystals was recrystallized from a mixed solvent of hexane and ethyl acetate, whereby colorless crystals were obtained.

후처리

  1. filtrationThe insoluble matter was filtered off from filtration through Celite
  2. concentrationThe filtrate was concentrated under reduced pressure
  3. additionThe concentrate was diluted with dichloromethane
  4. washwashed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe residue obtained
  7. distillationby distilling off the solvent under reduced pressure
  8. customwas purified by chromatography on a silica gel column (hexane:ethyl acetate 3:1)

출처 및 근거

ORD 기록
ord-86768dfe0fa94fcba8a489b9529fa2cf
출처 데이터셋
uspto-grants-2004_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06747023B1

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