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N-Methylcyclohexylamine → (S)-1,4-di(t-butoxycarbonyl)-2-(4-(N-cyclohexyl-N-methylamino)phenyl)piperazine

HRID 1784685
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HRID 1784685 반응식
Br[C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[CH2:13][N:12]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:11][CH2:10][N:9]2[C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])=[CH:4][CH:3]=1.[CH3:28][NH:29][CH:30]1[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]1.C(P(C(C)(C)C)C1C=CC=CC=1C1C=CC=CC=1)(C)(C)C.CC(C)([O-])C.[Na+]>C(O)(C)(C)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:24]([O:23][C:21]([N:9]1[CH2:10][CH2:11][N:12]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:13][C@@H:8]1[C:5]1[CH:6]=[CH:7][C:2]([N:29]([CH:30]2[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]2)[CH3:28])=[CH:3][CH:4]=1)=[O:22])([CH3:27])([CH3:26])[CH3:25]
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참가 물질

7

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HCID 7514N-MethylcyclohexylamineHCID 27342152-(Di-tert-butylphosphino)biphenylHCID 23676156Sodium t-butoxideHCID 53628944(S)-2-(4-bromophenyl)-1,4-di(t-butoxycarbonyl)piperazine

생성물 1

HCID 67117409(S)-1,4-di(t-butoxycarbonyl)-2-(4-(N-cyclohexyl-N-methylamino)phenyl)piperazine수율 70.4%

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 6386tert-Butanol용매

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온도
80 °C

실험 절차

A suspension of (S)-2-(4-bromophenyl)-1,4-di(t-butoxycarbonyl) piperazine (1.21 g, 2.75 mmol), N-methylcyclohexylamine (0.43 mL, 3.30 mmol), palladium acetate (25 mg, 0.11 mmol), 2-(di-t-butylphosphino)biphenyl (66 mg, 0.22 mmol), and sodium t-butoxide (370 mg, 3.85 mmol) in t-butanol (15 mL) was heated at 80° C. for 8 h. The resulting solution was partitioned between ethyl acetate and water. The organic layer was washed with brine, dried over anhydrous sodium sulfate, and concentrated in vacuo. The residue was purified by silica gel column chromatography eluting 10-15% ethyl acetate-hexane to afford (S)-1,4-di(t-butoxycarbonyl)-2-(4-(N-cyclohexyl-N-methylamino)phenyl)piperazine (917 mg) as white crystals.

후처리

  1. customThe resulting solution was partitioned between ethyl acetate and water
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by silica gel column chromatography
  6. washeluting 10-15% ethyl acetate-hexane

출처 및 근거

ORD 기록
ord-dddb005d28e743f6bebca0ca50f0b4f6
출처 데이터셋
uspto-grants-2009_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07504411B2

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