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4-(2-Methoxycarbonyl-phenyl)-piperidine-1-carboxylic acid tert-butyl ester → Tert-butyl 4-[2-(1-hydroxy-1-methyl ethyl)phenyl]piperidine-1-carboxylate

HRID 1627021
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HRID 1627021 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12]C(C2C=CC=CC=2C(OC)=O)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:24][Mg]Br.[C:27]1([CH3:33])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.[CH2:34]1[CH2:38][O:37]CC1>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:33]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[C:38]([OH:37])([CH3:34])[CH3:24])[CH2:12][CH2:13]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]
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참가 물질

5

반응물 3

HCID 111629634-(2-Methoxycarbonyl-phenyl)-piperidine-1-carboxylic acid tert-butyl esterHCID 22635083Tetrahydrofuran tolueneHCID 178418573HCID 178418573, 화합물

생성물 1

HCID 57459608Tert-butyl 4-[2-(1-hydroxy-1-methyl ethyl)phenyl]piperidine-1-carboxylate수율 69%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
45 °C

실험 절차

To a solution of 4-(2-Methoxycarbonyl-phenyl)-piperidine-1-carboxylic acid tert-butyl ester (2.6 g, 8.14 mmol) [C.A.S. 732275-95-5] in THF (150 ml) cooled at 0° C. and under nitrogen atmosphere, was added dropwise methylmagnesium bromide −1.4 M solution in toluene/THF (17.443 ml, 24.421 mmol) and the resulting reaction mixture was stirred at 45° C. for 2 h. After cooling in an ice bath the mixture was carefully quenched with a saturated aqueous solution of ammonium chloride, and then extracted with EtOAc. The combined organic phase was dried (Na2SO4) and the solvent evaporated in vacuo to yield D28 (2.77 g, 69%)

후처리

  1. customthe resulting reaction mixture
  2. temperatureAfter cooling in an ice bath the mixture
  3. customwas carefully quenched with a saturated aqueous solution of ammonium chloride
  4. extractionextracted with EtOAc
  5. dry with materialThe combined organic phase was dried (Na2SO4)
  6. customthe solvent evaporated in vacuo

출처 및 근거

ORD 기록
ord-eca53d50dce04b119a85f58b2b7299ed
출처 데이터셋
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08785486B2

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