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

HRID 1711220

반응식

HRID 1711220 반응식
[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]

참가 물질

7

반응물 3

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

생성물 1

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

시약·촉매·용매 3

HCID 962Water용매HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매

실험 절차

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 diethyl ester (iii).

후처리

  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

출처 및 근거

ORD 기록
ord-7a09d29648ba441496f25efeae018233
출처 데이터셋
uspto-grants-2010_09
특허 번호
US07790724B2

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