Benzyl Bromide → 2-Benzyl-1,4,5,6-tetrahydro-cyclopentapyrazole-3-carboxylic acid amide

HRID 475503ノート

反応式

HRID 475503 の反応式
[NH:1]1[C:5]2[CH2:6][CH2:7][CH2:8][C:4]=2[C:3]([C:9]([NH2:11])=[O:10])=[N:2]1.[OH-].[Na+].[CH2:14](Br)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C1COCC1>[CH2:14]([N:1]1[C:5]2[CH2:6][CH2:7][CH2:8][C:4]=2[C:3]([C:9]([NH2:11])=[O:10])=[N:2]1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[CH2:14]([N:2]1[CH:3]([C:9]([NH2:11])=[O:10])[C:4]2[CH2:8][CH2:7][CH2:6][C:5]=2[NH:1]1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

参加物

6

反応物 3

HCID 7498Benzyl BromideHCID 14798Sodium HydroxideHCID 451212581H,4H,5H,6H-cyclopenta[c]pyrazole-3-carboxamide

生成物 2

HCID 587136291-Benzyl-1,4,5,6-tetrahydro-cyclopentapyrazole-3-carboxylic acid amideHCID 693044772-Benzyl-1,4,5,6-tetrahydro-cyclopentapyrazole-3-carboxylic acid amide収率 196.4%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 1,4,5,6-tetrahydro-cyclopentapyrazole-3-carboxylic acid amide (41.5 g, 275 mmol) in THF (460 mL) at rt was added a solution of NaOH (5N aq., 110 mL, 0.54 mol). After stirring for 5 min benzyl bromide (49.2 g, 0.29 mol) was added and the reaction was stirred for 16 h. The volatiles were removed in vacuo and the resulting solid was washed with H2O (3×250 mL). Further concentration gave regioisomers of 1-benzyl-1,4,5,6-tetrahydro-cyclopentapyrazole-3-carboxylic acid amide and 2-benzyl-1,4,5,6-tetrahydro-cyclopentapyrazole-3-carboxylic acid amide (65.3 g, 270 mmol, 98% yield) as a 20:1 mixture and was used without separation).

後処理

  1. additionwas added
  2. customThe volatiles were removed in vacuo
  3. washthe resulting solid was washed with H2O (3×250 mL)
  4. concentrationFurther concentration

出典と根拠

ORDレコード
ord-82cb83c953dc4b479df7343cf5e60f7f
出典データセット
uspto-grants-2014_01
特許番号
US08637555B2

反応ノート

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