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Acetic Acid → (R)-N-[2-(4-Methoxybenzoylamino)-2-phenylethyl]-1-isopropylpiperidine-4-carboxamide

HRID 23957
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반응식

HRID 23957 반응식
FC(F)(F)C(O)=O.[CH3:8][O:9][C:10]1[CH:35]=[CH:34][C:13]([C:14]([NH:16][C@H:17]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH2:18][NH:19][C:20]([CH:22]2[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]2)=[O:21])=[O:15])=[CH:12][CH:11]=1.[CH3:36][C:37]([CH3:39])=O.C(O)(=O)C.C([BH3-])#N.[Na+].[NH4+].[OH-]>CO.C(Cl)Cl>[CH3:8][O:9][C:10]1[CH:11]=[CH:12][C:13]([C:14]([NH:16][C@H:17]([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH2:18][NH:19][C:20]([CH:22]2[CH2:27][CH2:26][N:25]([CH:37]([CH3:39])[CH3:36])[CH2:24][CH2:23]2)=[O:21])=[O:15])=[CH:34][CH:35]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 5

HCID 176Acetic AcidHCID 180AcetoneHCID 14923Ammonium HydroxideHCID 5003444Sodium cyanoborohydrideHCID 69592699(R)-N-[2-(4-Methoxybenzoylamino)-2-phenylethyl]piperidine-4-carboxamide trifluoroacetate

생성물 1

HCID 54102863(R)-N-[2-(4-Methoxybenzoylamino)-2-phenylethyl]-1-isopropylpiperidine-4-carboxamide
수율 70.8%

시약·촉매·용매 2

HCID 887Methanol용매3회HCID 6344Dichloromethane용매

실험 절차

(Alkylation Method A) (R)-N-[2-(4-Methoxybenzoylamino)-2-phenylethyl]piperidine-4-carboxamide trifluoroacetate (0.50 g, 1.0 mmol), acetone (4.5 mL, 61 mmol), acetic acid (0.28 mL, 4.9 mmol), and sodium cyanoborohydride (0.32 g, 5.1 mmol) were combined in methanol, and stirred. After 4 h, TLC (79% CH2Cl2, 19% methanol, 1% NH4OH) indicated reaction completion. The solution was diluted with methanol (100 mL), and passed through H+ form ion exchange resin (Varian SCX cartridge, Catalog #1225-6035) washed with methanol, and then with 2 M NH3 in methanol to collect the product. The product was recrystallized from methanol and ether to afford 0.30 g (70%) of a white crystalline solid

후처리

  1. customreaction completion
  2. customform ion exchange resin (Varian SCX cartridge, Catalog #1225-6035)
  3. washwashed with methanol
  4. customwith 2 M NH3 in methanol to collect the product
  5. customThe product was recrystallized from methanol and ether

출처 및 근거

ORD 기록
ord-0355da86d87b4cc396e86117d3587e5e
출처 데이터셋
uspto-grants-2005_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06855715B1

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