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

HRID 1711219

反応式

HRID 1711219 の反応式
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]

参加物

7

反応物 3

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

生成物 1

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

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-5b64d57edf6740d3b81f185e2a7dd28d
出典データセット
uspto-grants-2010_09
特許番号
US07790724B2

関連ノート

読み込み中…