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Imidazole → 1-(Benzyloxycarbonyl)-3-(tert-butyldimethylsilyloxymethyl)piperidine

HRID 602123
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HRID 602123 반응식
N1C=CN=C1.[Si:6](Cl)([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:8])[CH3:7].[CH2:14]([O:21][C:22]([N:24]1[CH2:29][CH2:28][CH2:27][CH:26]([CH2:30][OH:31])[CH2:25]1)=[O:23])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.O>CN(C)C=O>[CH2:14]([O:21][C:22]([N:24]1[CH2:29][CH2:28][CH2:27][CH:26]([CH2:30][O:31][Si:6]([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:8])[CH3:7])[CH2:25]1)=[O:23])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 795ImidazoleHCID 962WaterHCID 28928tert-Butyldimethylsilyl chlorideHCID 2776577Benzyl 3-(hydroxymethyl)piperidine-1-carboxylate

생성물 1

HCID 589926311-(Benzyloxycarbonyl)-3-(tert-butyldimethylsilyloxymethyl)piperidine수율 99%

시약·촉매·용매 1

HCID 6228
Dimethylformamide
용매

실험 절차

Imidazole (3.00 g, 44.0 mmol) and tert-butyldimethylsilyl chloride (6.63 g, 44.0 mmol) were added to 1-(benzyloxycarbonyl)piperidin-3-yl methanol (9.15 g, 36.7 mmol) in N,N-dimethylformamide (40 mL). The solution was stirred at room temperature for 6 hours. Subsequently, water was added and the mixture was extracted with ethyl acetate. The extract washed with brine and was dried over magnesium sulfate, followed by evaporation of the solvent. Purification of the residue by silica gel column chromatography (hexane:ethyl acetate=20:1->5:1) gave 13.2 g (99%) of the desired compound as a colorless oil.

후처리

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract washed with brine
  3. dry with materialwas dried over magnesium sulfate
  4. customfollowed by evaporation of the solvent
  5. customPurification of the residue by silica gel column chromatography (hexane:ethyl acetate=20:1->5:1)

출처 및 근거

ORD 기록
ord-cb168814464c40849f6e4caa3ca11a9f
출처 데이터셋
uspto-grants-2011_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07902367B2

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