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Triethylamine → {2-[3,5-Diethyl-1-(2,4,6-trimethylphenyl)-1H-pyrazol-4-ylmethyl]-1,2,3,4-tetrahydroisoquinolin-3-yl}methanol

HRID 725278
ノート
印刷プレビュー

反応式

HRID 725278 の反応式
[CH2:1]([C:3]1[C:7]([CH2:8]O)=[C:6]([CH2:10][CH3:11])[N:5]([C:12]2[C:17]([CH3:18])=[CH:16][C:15]([CH3:19])=[CH:14][C:13]=2[CH3:20])[N:4]=1)[CH3:2].C(N(CC)CC)C.CS(Cl)(=O)=O.[OH:33][CH2:34][CH:35]1[CH2:44][C:43]2[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=2)[CH2:37][NH:36]1>C(Cl)Cl.C(#N)C.CN(C)C=O.O>[CH2:1]([C:3]1[C:7]([CH2:8][N:36]2[CH:35]([CH2:34][OH:33])[CH2:44][C:43]3[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=3)[CH2:37]2)=[C:6]([CH2:10][CH3:11])[N:5]([C:12]2[C:17]([CH3:18])=[CH:16][C:15]([CH3:19])=[CH:14][C:13]=2[CH3:20])[N:4]=1)[CH3:2]
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 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 3752277(1,2,3,4-Tetrahydro-isoquinolin-3-yl)-methanolHCID 218373233,5-Diethyl-1-(2,4,6-trimethylphenyl)pyrazole-4-methanol

生成物 1

HCID 67553028{2-[3,5-Diethyl-1-(2,4,6-trimethylphenyl)-1H-pyrazol-4-ylmethyl]-1,2,3,4-tetrahydroisoquinolin-3-yl}methanol収率 44.1%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6344Dichloromethane溶媒HCID 21891449acetonitrile N,N-dimethylformamide溶媒

反応条件

温度
0 °C

実験手順

To a solution of 272 mg (1.0 mmol) of 3,5-diethyl-1-(2,4,6-trimethylphenyl)pyrazole-4-methanol in 5 mL of methylene chloride cooled to 0° C. under dry nitrogen in a 25 mL 3-neck flask, was added to 0.2 mL (2.5 mmol) of triethylamine and 0.092 mL (2.0 mmol) of methanesulfonyl chloride. This mixture was stirred for 15 minutes at 0° C. and then 0.648 g (4.0 mmol) of (+)-3-hydroxymethyl-1,2,3,4-tetrahydroisoquinoline in 1 mL of 50:50 dimethylformamide acetonitrile was added. The reaction mixture was heated at reflux overnight whereupon no starting material was seen by TLC. The cooled reaction mixture was diluted with water and the product was extracted with ethyl acetate. After drying (brine wash, magnesium sulfate) and evaporation, the crude product was chromatographed on silica gel, eluting with 10:1 and 5:1 hexane/ethyl acetate to give 184 mg (44%) of the desired product. 1H-NMR (CDCl3):0.80 (3H, t, J=7), 1.18 (3H, t, J=7), 1.92 (6H, s), 2.21 (2H, q, J=7), 2.28 (3H, s), 2.55 (2H, q, J=7), 2.97 (2H, d of d, J=7), 3.25 (1H, m), 3.50-3.66 (5H, m), 3.80 (2H, d, J=12), 6.82-7.16 (6H, m).

後処理

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux overnight whereupon no starting material
  3. customThe cooled reaction mixture
  4. extractionthe product was extracted with ethyl acetate
  5. customAfter drying
  6. wash(brine wash, magnesium sulfate) and evaporation
  7. customthe crude product was chromatographed on silica gel
  8. washeluting with 10:1 and 5:1 hexane/ethyl acetate

出典と根拠

ORDレコード
ord-3c44f0bc0c8e4fa1915a69eb0bf5a4ce
出典データセット
uspto-grants-1998_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05705646

反応ノート

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