Potassium ethoxide → 3-(2-Nitro-3-piperidin-1-yl-phenyl)-2,5-dioxo-hexanedioic acid di ethyl ester

HRID 33473

反応式

HRID 33473 の反応式
[CH2:1]([O:3][C:4](=[O:23])[C:5](=[O:22])[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([N:13]2[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)[C:8]=1[N+:19]([O-:21])=[O:20])[CH3:2].[O-]CC.[K+].[C:28]([O:33][CH2:34][CH2:35]Br)(=[O:32])[C:29]([CH3:31])=[O:30]>C1COCC1.O.CCOCC>[CH2:1]([O:3][C:4](=[O:23])[C:5](=[O:22])[CH:6]([C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([N:13]2[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]2)[C:8]=1[N+:19]([O-:21])=[O:20])[CH2:31][C:29](=[O:30])[C:28]([O:33][CH2:34][CH3:35])=[O:32])[CH3:2]

参加物

7

反応物 3

HCID 23670592Potassium ethoxideHCID 597967713-(2-Nitro-3-piperidin-1-yl-phenyl)-2-oxo-propionic acid ethyl esterHCID 86587973Bromoethyl pyruvate

生成物 1

HCID 597967863-(2-Nitro-3-piperidin-1-yl-phenyl)-2,5-dioxo-hexanedioic acid di ethyl ester

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of 3-(2-nitro-3-piperidin-1-yl-phenyl)-2-oxo-propionic acid ethyl ester (ii) in THF is treated with potassium ethoxide (“KOEt”) (1 eq), followed by bromoethyl pyruvate (1.05 eq), at 0° C. The reaction is allowed to warm to room temperature over 90 min. The reaction is diluted with water and ether, partitioned, and the aqueous layer is washed with ether. The combined organic layers are dried over MgSO4, filtered and concentrated. Chromatography gives 3-(2-nitro-3-piperidin-1-yl-phenyl)-2,5-dioxo-hexanedioic acid di ethyl ester (iii).

後処理

  1. custompartitioned
  2. washthe aqueous layer is washed with ether
  3. dry with materialThe combined organic layers are dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-e690c206e68c445d9f0bccfcc72a2c1e
出典データセット
uspto-grants-2008_09
特許番号
US07429603B2

関連ノート

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