Triethylamine → Methanesulfonic acid 2-[2-(4-chloro-phenyl)-2,4,5,6-tetrahydro-cyclopentapyrazol-3-yl]-2-cyclohexyl-ethyl ester

HRID 889380ノート

反応式

HRID 889380 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([CH:13]([CH:16]3[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]3)[CH2:14][OH:15])=[C:11]3[CH2:22][CH2:23][CH2:24][C:10]3=[N:9]2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[S:32](Cl)([CH3:35])(=[O:34])=[O:33]>ClCCl.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:12]([CH:13]([CH:16]3[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]3)[CH2:14][O:15][S:32]([CH3:35])(=[O:34])=[O:33])=[C:11]3[CH2:22][CH2:23][CH2:24][C:10]3=[N:9]2)=[CH:6][CH:7]=1

参加物

6

反応物 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 673874592-(2-(4-Chlorophenyl)-2,4,5,6-tetrahydrocyclopenta[C]pyrazol-3-YL)-2-cyclohexylethanol

生成物 1

HCID 86657984Methanesulfonic acid 2-[2-(4-chloro-phenyl)-2,4,5,6-tetrahydro-cyclopentapyrazol-3-yl]-2-cyclohexyl-ethyl ester収率 81%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
25 °C

実験手順

To a solution of 2-[2-(4-chloro-phenyl)-2,4,5,6-tetrahydro-cyclopentapyrazol-3-yl]-2-cyclohexyl-ethanol (250 mg, 0.72 mmol; example 1.4) in dry dichloromethane (5 ml) was added triethylamine (0.32 ml, 1.19 mmol) at 25° C. Mesyl chloride (0.16 ml, 0.725 mmol) was added dropwise at 0° C. The reaction mixture was allowed to stir at 25° C. for 2 h, diluted with water (5 ml), and the aqueous layer was extracted with dichloromethane (3×10 ml). The combined organic layers were washed sequentially with ice water (10 ml), 10% aqueous NaHCO3 solution (10 ml), brine (10 ml) and finally dried over Na2SO4. The solvent was removed under reduced pressure to give the title compound as light yellow oil (250 mg, 0.58 mmol; 81%), which was sufficiently pure to be used in the next reaction step.

後処理

  1. extractionthe aqueous layer was extracted with dichloromethane (3×10 ml)
  2. washThe combined organic layers were washed sequentially with ice water (10 ml), 10% aqueous NaHCO3 solution (10 ml), brine (10 ml)
  3. dry with materialfinally dried over Na2SO4
  4. customThe solvent was removed under reduced pressure

出典と根拠

ORDレコード
ord-321531dbdda149edaa7bc1678b0ee5d5
出典データセット
uspto-grants-2012_08
特許番号
US08252826B2

反応ノート

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