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Triphenylphosphine → 4-Methyl-4-(2-trifluoromethylphenoxy)piperidine

HRID 552141
ノート
印刷プレビュー

反応式

HRID 552141 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([OH:15])([CH3:14])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[C:23]([F:26])([F:25])[F:24].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1(C)C=CC=CC=1>[CH3:14][C:11]1([O:15][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[C:23]([F:26])([F:25])[F:24])[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]1.[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([CH3:14])([O:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[C:23]([F:24])([F:25])[F:26])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]
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 4

HCID 11776TriphenylphosphineHCID 679582-TrifluoromethylphenolHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 227308121-Boc-4-methyl-piperidin-4-OL

生成物 2

HCID 671715074-Methyl-4-(2-trifluoromethylphenoxy)piperidineHCID 671718194-Methyl-4-(2-trifluoromethylphenoxy)piperidine-1-carboxylic acid tert-butyl ester

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

To a stirred solution of 4-hydroxy-4-methylpiperidine-1-carboxylic acid tert-butyl ester (0.500 g, 2.32 mmol) in toluene (10 mL) was added 2-hydroxybenzotrifluoride (0.414 g, 2.56 mmol), triphenylphosphine (0.682 g, 2.555 mmol) and diethyl azocarboxylate (0.5 mL, 2.56 mmol). The resulting mixture was stirred at reflux for 18 hours. Toluene was removed in vacuo and the obtained crude product was purified by column chromatography to yield the desired product, 4-methyl-4-(2-trifluoromethyl-phenoxy)piperidine-1-carboxylic acid tert-butyl ester, in 5% yield (0.025 g). 1H NMR (300 MHz, CDCl3) δ 7.57-7.54 (m, 1H), 7.41-7.36 (m, 1H), 7.09 (d, J=7.9 Hz, 1H), 7.02-6.97 (m, 1H), 3.81-3.76 (m, 2H), 3.28 (t, J=11.9 Hz, 2H), 2.15-2.11 (m, 2H), 1.67-1.58 (m, 2H), 1.44 (s, 9H), 1.39 (s, 3H).

後処理

  1. temperatureat reflux for 18 hours
  2. customToluene was removed in vacuo
  3. customthe obtained crude product
  4. customwas purified by column chromatography

出典と根拠

ORDレコード
ord-f14273d3edce4387ab57b9a1ac94a29d
出典データセット
uspto-grants-2011_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07951805B2

反応ノート

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