Cyclohexanone → benzyl 3-(5-amino-4-cyclohex-1-enyl-1-methyl-1H-pyrazol-3-yl)pyrrolidine-1-carboxylate

HRID 1034958ノート

反応式

HRID 1034958 の反応式
[NH2:1][C:2]1[N:6]([CH3:7])[N:5]=[C:4]([CH:8]2[CH2:12][CH2:11][N:10]([C:13]([O:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[O:14])[CH2:9]2)[CH:3]=1.[C:23]1(=O)[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1>C(O)(=O)C>[NH2:1][C:2]1[N:6]([CH3:7])[N:5]=[C:4]([CH:8]2[CH2:12][CH2:11][N:10]([C:13]([O:15][CH2:16][C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)=[O:14])[CH2:9]2)[C:3]=1[C:23]1[CH2:28][CH2:27][CH2:26][CH2:25][CH:24]=1

参加物

4

反応物 2

HCID 7967CyclohexanoneHCID 69162082benzyl 3-(5-amino-1-methyl-1H-pyrazol-3-yl)-pyrrolidine-1-carboxylate

生成物 1

HCID 69162390benzyl 3-(5-amino-4-cyclohex-1-enyl-1-methyl-1H-pyrazol-3-yl)pyrrolidine-1-carboxylate収率 53%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

A solution of EXAMPLE 24C (1.78 g, 5.92 mmol) and cyclohexanone (1.23 mL, 11.85 mmol) in acetic acid (10 mL) was stirred at ambient temperature overnight and at 55° C. for 1 day. The acetic acid was removed and the residue partitioned between sodium bicarbonate solution and ethyl acetate. The organic phase was washed with water, concentrated and the residue purified by flash chromatography on silica gel using 70-90% ethyl acetate in hexane to provide the title compound as a light yellow solid (1.19 g, 53%). MS (DCI): m/z 381 (M+H)+.

後処理

  1. customThe acetic acid was removed
  2. customthe residue partitioned between sodium bicarbonate solution and ethyl acetate
  3. washThe organic phase was washed with water
  4. concentrationconcentrated
  5. customthe residue purified by flash chromatography on silica gel using 70-90% ethyl acetate in hexane

出典と根拠

ORDレコード
ord-524120b59ee94e51a667fd2808e326fb
出典データセット
uspto-grants-2013_10
特許番号
US08546368B2

反応ノート

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