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

HRID 475501ノート

反応式

HRID 475501 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.C([O-])([O-])=O.[K+].[K+].[CH2:18](Br)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>CN(C=O)C.CCOC(C)=O>[CH2:18]([N:2]1[C:3]([C:9]([NH2:11])=[O:10])=[C:4]2[CH2:8][CH2:7][CH2:6][C:5]2=[N:1]1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

参加物

6

反応物 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 451212581H,4H,5H,6H-cyclopenta[c]pyrazole-3-carboxamide

生成物 1

HCID 587136472-Benzyl-2,4,5,6-tetrahydro-cyclopentapyrazole-3-carboxylic acid amide収率 18.1%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a stirring solution of 1,4,5,6-tetrahydro-cyclopentapyrazole-3-carboxylic acid amide (2.57 g, 17.0 mmol) in DMF (34 mL) at 25° C. was added K2CO3 (5.87 g, 42.5 mmol) followed by benzyl bromide (4.36 g g, 25.5 mmol). The reaction was stirred at ambient temperature for 16 h at which time the mixture was diluted with EtOAc (75 mL) and filtered. The filtrate was washed with H2O (100 mL) and the aqueous phase was back-extracted with EtOAc (75 mL) and CH2Cl2 (75 mL). The combined organic extracts were dried over MgSO4, filtered, and concentrated in vacuo. Purification by silica gel chromatography (50% EtOAc in hexanes gradient to 95% EtOAc in hexanes) gave 2-benzyl-2,4,5,6-tetrahydro-cyclopentapyrazole-3-carboxylic acid amide (739 mg, 3.07 mmol, 18% yield) isolated as a white solid followed by 1-benzyl-1,4,5,6-tetrahydro-cyclopentapyrazole-3-carboxylic acid amide (3.24 g, 13.4 mmol, 79% yield) isolated as a white solid.

後処理

  1. filtrationfiltered
  2. washThe filtrate was washed with H2O (100 mL)
  3. extractionthe aqueous phase was back-extracted with EtOAc (75 mL) and CH2Cl2 (75 mL)
  4. dry with materialThe combined organic extracts were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification by silica gel chromatography (50% EtOAc in hexanes gradient to 95% EtOAc in hexanes)

出典と根拠

ORDレコード
ord-614abc68c85742719d31fd47f54b3dc9
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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