Diethyl Oxalate → 3-(2-Nitro-3-piperidin-1-yl-phenyl)-2-oxo-propionic acid ethyl ester

HRID 1711219

반응식

HRID 1711219 반응식
C[CH:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[CH:12][C:11](CO)=[CH:10][C:9]=2[N+:16]([O-:18])=[O:17])[CH2:4][CH2:3]1.[CH:19]([N-]C(C)C)(C)C.[Li+].[C:27]([O:34][CH2:35][CH3:36])(=[O:33])[C:28](OCC)=[O:29]>C1COCC1.O.CCOCC>[CH2:35]([O:34][C:27](=[O:33])[C:28](=[O:29])[CH2:19][C:10]1[CH:11]=[CH:12][CH:13]=[C:8]([N:5]2[CH2:4][CH2:3][CH2:2][CH2:7][CH2:6]2)[C:9]=1[N+:16]([O-:18])=[O:17])[CH3:36]

참가 물질

7

반응물 3

HCID 7268Diethyl OxalateHCID 2724682Lithium diisopropylamideHCID 28963353(4-(4-Methylpiperidin-1-yl)-3-nitrophenyl)methanol

생성물 1

HCID 597967713-(2-Nitro-3-piperidin-1-yl-phenyl)-2-oxo-propionic acid ethyl ester

시약·촉매·용매 3

HCID 962Water용매HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매

실험 절차

A solution of 1-(3-methyl-2-nitro-phenyl)-piperidine (i) in THF is treated with lithium diisopropylamide (“LDA”) (1 eq), followed by diethyl oxalate (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-oxo-propionic acid ethyl ester (ii).

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-5b64d57edf6740d3b81f185e2a7dd28d
출처 데이터셋
uspto-grants-2010_09
특허 번호
US07790724B2

연결된 노트

불러오는 중…