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Sodium Iodide → (+/-)-Methyl(cis)-1-(4-isopropylbenzyl)-2-[4-(trifluoromethyl)phenyl]piperidine-4-carboxylate

HRID 1869743
ノート
印刷プレビュー

反応式

HRID 1869743 の反応式
[F:1][C:2]([F:20])([F:19])[C:3]1[CH:8]=[CH:7][C:6]([C@H:9]2[CH2:14][C@@H:13]([C:15]([O:17][CH3:18])=[O:16])[CH2:12][CH2:11][NH:10]2)=[CH:5][CH:4]=1.[CH:21]([C:24]1[CH:31]=[CH:30][C:27]([CH2:28]Br)=[CH:26][CH:25]=1)([CH3:23])[CH3:22].[Na+].[I-].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.CCOC(C)=O.O>[CH:21]([C:24]1[CH:31]=[CH:30][C:27]([CH2:28][N:10]2[CH2:11][CH2:12][C@H:13]([C:15]([O:17][CH3:18])=[O:16])[CH2:14][C@@H:9]2[C:6]2[CH:5]=[CH:4][C:3]([C:2]([F:19])([F:1])[F:20])=[CH:8][CH:7]=2)=[CH:26][CH:25]=1)([CH3:23])[CH3:22]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 477191-(Bromomethyl)-4-(propan-2-yl)benzeneHCID 86617995Methyl(cis)-2-[4-(trifluoromethyl)phenyl]piperidine-4-carboxylate

生成物 1

HCID 86617994(+/-)-Methyl(cis)-1-(4-isopropylbenzyl)-2-[4-(trifluoromethyl)phenyl]piperidine-4-carboxylate収率 81%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
150 °C

実験手順

Methyl(cis)-2-[4-(trifluoromethyl)phenyl]piperidine-4-carboxylate (0.22 g), 4-isopropylbenzyl bromide (240 mg), NaI (15 mg), K2CO3 (287 mg) in DMF (2 ml) were placed in a microwave tube and the contents were heated in the microwave oven for 20 min at 150° C. The cooled mixture was dispersed between H2O and EtOAc and the organic extracts were washed with brine, dried (MgSO4) and evaporated. The crude oil was purified by chromatography on silica using 5-8% EtOAc in hexane to yield a colourless oil (260 mg, 81%) which crystallized on standing. 1H NMR (400 MHz, CDCl3) δ: 1.23 (6H, d, J 6.9), 1.71-1.81 (2H, m), 1.92 (1H, d, J 12.9), 1.97-2.04 (2H, m), 2.44-2.50 (1H, m), 2.82-2.90 (2H, m), 3.08-3.10 (1H, m), 3.25 (1H, dd, J 2.8, 11.3), 3.66 (4H, t, J 9.1), 7.14 (4H, q, J 6.3), 7.58 (4H, s); M/Z (ES+) 420 (MH+).

後処理

  1. washthe organic extracts were washed with brine
  2. dry with materialdried (MgSO4)
  3. customevaporated
  4. customThe crude oil was purified by chromatography on silica using 5-8% EtOAc in hexane

出典と根拠

ORDレコード
ord-152469e75d9748a68f194f2fe7ef0b05
出典データセット
uspto-grants-2009_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07638629B2

反応ノート

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