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Piperidine → (2S)-2-(4-piperidin-1-yl-phenyl)-piperazine-1,4-dicarboxylic acid di-tert-butyl ester

HRID 1091352
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HRID 1091352 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][C@@H:9]1[C:21]1[CH:26]=[CH:25][C:24](Br)=[CH:23][CH:22]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH:28]1[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1.CC(C)([O-])C.[Na+].C(P(C(C)(C)C)C1C=CC=CC=1C1C=CC=CC=1)(C)(C)C>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(OCC)(=O)C.O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][C@@H:9]1[C:21]1[CH:26]=[CH:25][C:24]([N:28]2[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]2)=[CH:23][CH:22]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

9

반응물 4

HCID 8082PiperidineHCID 27342152-(Di-tert-butylphosphino)biphenylHCID 23676156Sodium t-butoxideHCID 53628944(S)-2-(4-bromophenyl)-1,4-di(t-butoxycarbonyl)piperazine

생성물 1

HCID 66594922(2S)-2-(4-piperidin-1-yl-phenyl)-piperazine-1,4-dicarboxylic acid di-tert-butyl ester수율 43%

시약·촉매·용매 4

HCID 167845palladium(II) acetate촉매
HCID 962Water용매
HCID 1140Toluene용매
HCID 8857Ethyl Acetate용매

실험 절차

A solution of (2S)-2-(4-bromophenyl)-piperazine-1,4-dicarboxylic acid di-tert-butyl ester (1.06 g, 2.40 mmol), piperidine (0.29 ml, 2.88 mmol), palladium acetate (22.0 mg, 0.096 mmol), sodium tert-butoxide (323 mg, 3.36 mmol) and 2-(di-t-butylphosphino)biphenyl (57.0 mg, 0.192 mmol) in toluene (16 ml) was stirred at 80° C. for 6 hours. Water and ethyl acetate were added to the solution and the solution was passed through Celite column. The whole was extracted with ethyl acetate and the organic lawyer was washed with brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give (2S)-2-(4-piperidin-1-yl-phenyl)-piperazine-1,4-dicarboxylic acid di-tert-butyl ester (455 mg, 43%) as white crystals.

후처리

  1. extractionThe whole was extracted with ethyl acetate
  2. washthe organic lawyer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate)

출처 및 근거

ORD 기록
ord-124d30efdfcc466abbd130c98011a1ac
출처 데이터셋
uspto-grants-2012_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08129377B2

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