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

HRID 23957
ノート
印刷プレビュー

反応式

HRID 23957 の反応式
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
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 5

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 887Methanol溶媒3 回HCID 6344Dichloromethane溶媒

実験手順

(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

後処理

  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

出典と根拠

ORDレコード
ord-0355da86d87b4cc396e86117d3587e5e
出典データセット
uspto-grants-2005_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06855715B1

反応ノート

読み込み中…

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