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4-Fluorophenol → N-tert-butyloxycarbonyl4-(p-fluorophenoxymethyl)piperidine

HRID 413270
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HRID 413270 반응식
N(C(OCC)=O)=NC(OCC)=O.[C:13]([O:17][C:18]([N:20]1[CH2:25][CH2:24][CH:23]([CH2:26][OH:27])[CH2:22][CH2:21]1)=[O:19])([CH3:16])([CH3:15])[CH3:14].[F:28][C:29]1[CH:34]=[CH:33][C:32](O)=[CH:31][CH:30]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[C:13]([O:17][C:18]([N:20]1[CH2:25][CH2:24][CH:23]([CH2:26][O:27][C:32]2[CH:33]=[CH:34][C:29]([F:28])=[CH:30][CH:31]=2)[CH2:22][CH2:21]1)=[O:19])([CH3:16])([CH3:15])[CH3:14]
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참가 물질

6

반응물 4

HCID 97324-FluorophenolHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 2764081Tert-butyl 4-(hydroxymethyl)piperidine-1-carboxylate

생성물 1

HCID 15512457N-tert-butyloxycarbonyl4-(p-fluorophenoxymethyl)piperidine

시약·촉매·용매 1

HCID 8028
Tetrahydrofuran
용매

실험 절차

Over the course of 30 minutes, 10.5 ml of diethyl azodicarboxylate are poured onto a mixture of 13.5 g of N-tert-butyloxycarbonyl-4-hydroxymethylpiperidine, 7.45 g of p-fluorophenol, 17.4 g of triphenylphosphine and 140 ml of tetrahydrofuran. After stirring for 12 hours at ambient temperature, the reaction mixture is concentrated, taken up in ether, washed with water and then 1N sodium hydroxide solution, and then washed with water. After drying, filtration and evaporation under reduced pressure, chromatography over silica gel (cyclohexane/ethyl acetate: 90/10) allows the expected product to be isolated.

후처리

  1. concentrationthe reaction mixture is concentrated
  2. washwashed with water
  3. wash1N sodium hydroxide solution, and then washed with water
  4. customAfter drying
  5. filtrationfiltration and evaporation under reduced pressure, chromatography over silica gel (cyclohexane/ethyl acetate: 90/10)
  6. customto be isolated

출처 및 근거

ORD 기록
ord-2cef51f8c8024ac0bcff6a9554704444
출처 데이터셋
uspto-grants-2003_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06566364B2

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