Ammonium cerium (IV) nitrate → Acetic acid 4-oxo-4,5,6,7-tetrahydro-pyrazolo[1,5-a]pyrazin-2-ylmethyl ester

HRID 2046214ノート

反応式

HRID 2046214 の反応式
[N+]([O-])([O-])=O.[Ce+4].[NH4+].[N+]([O-])([O-])=O.[N+]([O-])([O-])=O.[N+]([O-])([O-])=O.[N+]([O-])([O-])=O.COC1C=CC(C[N:30]2[CH2:35][CH2:34][N:33]3[N:36]=[C:37]([CH2:39][O:40][C:41](=[O:43])[CH3:42])[CH:38]=[C:32]3[C:31]2=[O:44])=CC=1>O.C(#N)C>[O:44]=[C:31]1[NH:30][CH2:35][CH2:34][N:33]2[N:36]=[C:37]([CH2:39][O:40][C:41](=[O:43])[CH3:42])[CH:38]=[C:32]12

参加物

5

反応物 2

HCID 9869224Ammonium cerium (IV) nitrateHCID 67975764Acetic acid 5-(4-methoxy-benzyl)-4-oxo-4,5,6,7-tetrahydro-pyrazolo[1,5-a]pyrazin-2-ylmethyl ester

生成物 1

HCID 67974158Acetic acid 4-oxo-4,5,6,7-tetrahydro-pyrazolo[1,5-a]pyrazin-2-ylmethyl ester収率 62.3%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6342Acetonitrile溶媒

実験手順

A solution of ammonium cerium (IV) nitrate (0.7 g, 1.29 mmol) in water (1.1 mL) was added to a stirred solution of acetic acid 5-(4-methoxy-benzyl)-4-oxo-4,5,6,7-tetrahydro-pyrazolo[1,5-a]pyrazin-2-ylmethyl ester (142 mg, 0.43 mmol) in ACN (4.3 mL). The mixture was stirred at room temperature for 30 minutes and the solvents evaporated in vacuo. The crude product was purified by flash column chromatography (silica, 7 N solution of ammonia in MeOH in DCM 0/100 to 10/90). The desired fractions were collected and concentrated in vacuo to yield acetic acid 4-oxo-4,5,6,7-tetrahydro-pyrazolo[1,5-a]pyrazin-2-ylmethyl ester (56 mg, 62% yield) as a white solid.

後処理

  1. customthe solvents evaporated in vacuo
  2. customThe crude product was purified by flash column chromatography (silica, 7 N solution of ammonia in MeOH in DCM 0/100 to 10/90)
  3. customThe desired fractions were collected
  4. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-0635435dcb23452e8f829673803a4dfc
出典データセット
uspto-grants-2013_11
特許番号
US08592422B2

反応ノート

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