Cyclohexane → HCID 57545992、化合物

HRID 913844

反応式

HRID 913844 の反応式
ClC(Cl)(Cl)C(=N)O[CH:5]([C:7]1[CH:8]=[C:9]([Br:24])[CH:10]=[C:11]2[C:15]=1[N:14]([CH2:16][O:17][CH2:18][CH2:19][Si:20]([CH3:23])([CH3:22])[CH3:21])[N:13]=[CH:12]2)[CH3:6].[F:28][C:29]1[CH:34]=[CH:33][C:32]([C:35]2([CH2:48][OH:49])[CH2:40][CH2:39][N:38]([C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42])[CH2:37][CH2:36]2)=[CH:31][CH:30]=1.C1CCCCC1>ClCCl>[Br:24][C:9]1[CH:10]=[C:11]2[C:15](=[C:7]([CH:5]([O:49][CH2:48][C:35]3([C:32]4[CH:31]=[CH:30][C:29]([F:28])=[CH:34][CH:33]=4)[CH2:36][CH2:37][N:38]([C:41]([O:43][C:44]([CH3:45])([CH3:46])[CH3:47])=[O:42])[CH2:39][CH2:40]3)[CH3:6])[CH:8]=1)[N:14]([CH2:16][O:17][CH2:18][CH2:19][Si:20]([CH3:22])([CH3:21])[CH3:23])[N:13]=[CH:12]2

参加物

5

反応物 3

HCID 8078CyclohexaneHCID 19084679Tert-butyl 4-(4-fluorophenyl)-4-(hydroxymethyl)piperidine-1-carboxylateHCID 57546156HCID 57546156、化合物

生成物 1

HCID 57545992HCID 57545992、化合物

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of (±)-1-(5-bromo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indazol-7-yl)ethyl 2,2,2-trichloroacetimidate (780 mg, 1.512 mmol) and tert-butyl 4-(4-fluorophenyl)-4-(hydroxymethyl)piperidine-1-carboxylate (468 mg, 1.512 mmol) in dichloromethane (3 mL) at 0° C. was added cyclohexane (3 mL) and tetrafluoroboric acid diethyl etherate (0.041 mL, 0.302 mmol). After 15 min, the reaction was quenched by addition of triethylamine (ca. 0.05 mL). The reaction was diluted with diethyl ether, washed with water (2×), then brine, dried over magnesium sulfate, and concentrated. Column chromatography (12%→18% EtOAc/Hex) gave 543 mg (54%) as a colorless film. 1H-NMR (CDCl3, 500 MHz) δ 7.87 (s, 1H), 7.71 (d, J=1.8, 1H), 7.21 (m, 2H), 7.18 (s, 1H), 6.97 (m, 2H), 5.58 (qAB, JAB, 11.6, 2H), 5.06 (q, J=6.1, 1H), 3.68 (m, 2H), 3.41 (m, 2H), 3.24 (qAB, JAB=8.9, 2H), 3.02 (m, 2H), 2.12 (m, 1H), 2.04 (m, 1H), 1.83 (m, 2H), 1.42 (s, 12H), 0.80 (m, 1H), 0.71 (m, 1H), −0.11 (s, 9H); 13C NMR (126 MHz, CDCl3) δ ppm 162.4, 160.4, 155.0, 138.6, 136.1, 133.4, 129.3, 128.7 (d, J=7.7), 128.1, 127.4, 122.5, 115.3, 115.1, 114.8, 79.8, 79.4, 76.7, 72.8, 66.1, 41.1, 40.0 (br), 32.3, 32.1, 28.6, 22.8, 17.9, −1.4. Mass spec.: 662.02 (MH)+.

後処理

  1. customthe reaction was quenched by addition of triethylamine (ca. 0.05 mL)
  2. additionThe reaction was diluted with diethyl ether
  3. washwashed with water (2×)
  4. dry with materialbrine, dried over magnesium sulfate
  5. concentrationconcentrated
  6. customColumn chromatography (12%→18% EtOAc/Hex) gave 543 mg (54%) as a colorless film

出典と根拠

ORDレコード
ord-10d19ba49d3b462781f18cbb0a089aee
出典データセット
uspto-grants-2011_09
特許番号
US08026257B2

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