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Thiophene → (+/-)-1,1-Dimethylethyl 4-[4-(acetylamino)-4-phenyl-1-piperidinyl]-2-(phenylmethyl)-1-piperidinecarboxylate

HRID 1699466
ノート
印刷プレビュー

反応式

HRID 1699466 の反応式
O=[C:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH:4]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:3]1.[C:22]1([C:28]2([NH:34][C:35](=[O:37])[CH3:36])[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]2)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.S1C=CC=C1>CC(O)C.[Pt].CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-]>[C:35]([NH:34][C:28]1([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:29][CH2:30][N:31]([CH:2]2[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH:4]([CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:3]2)[CH2:32][CH2:33]1)(=[O:37])[CH3:36]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 3

HCID 8030ThiopheneHCID 15886675N-(4-Phenylpiperidin-4-yl)acetamideHCID 183199211-Boc-2-benzylpiperidin-4-one

生成物 1

HCID 18319927(+/-)-1,1-Dimethylethyl 4-[4-(acetylamino)-4-phenyl-1-piperidinyl]-2-(phenylmethyl)-1-piperidinecarboxylate収率 81.4%

試薬・触媒・溶媒 3

HCID 11026Titanium isopropoxide触媒
HCID 23939Platinum触媒
HCID 3776Isopropanol溶媒

実験手順

A mixture of (±)-1,1-dimethylethyl 4-oxo-2-(phenylmethyl)-1-piperidine carboxylate (0.1 mol) and N-(4-phenyl-4-piperidinyl)acetamide (0.1 mol) in 2-propanol (500 ml) was hydrogenated at 50° C. with platinum (4 g) as a catalyst in the presence of titanium(IV)isopropoxide (28.5 g) and thiophene (4%; 1 ml). After uptake of hydrogen, the catalyst was filtered off and the filtrate was evaporated. The residue was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH 97/3). The pure fractions were collected and the solvent was evaporated, yielding 40 g (74.1%) of (±)-1,1-dimethylethyl 4-[4-(acetylamino)-4-phenyl-1-piperidinyl]-2-(phenylmethyl)-1-piperidinecarboxylate (intermediate 19).

後処理

  1. filtrationAfter uptake of hydrogen, the catalyst was filtered off
  2. customthe filtrate was evaporated
  3. customThe residue was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH 97/3)
  4. customThe pure fractions were collected
  5. customthe solvent was evaporated

出典と根拠

ORDレコード
ord-7c48eb962fe540b793deef9d5ad6d414
出典データセット
uspto-grants-2002_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06346540B1

反応ノート

読み込み中…

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