Acetic Acid → 4-Oxo-6-piperidin-1-yl-4,5-dihydro-furo[2,3-c]quinoline-2-carboxylic acid ethyl ester

HRID 33474ノート

反応式

HRID 33474 の反応式
C([O:3][C:4](=O)[C:5](=[O:30])[CH:6]([C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([N:21]2[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]2)[C:16]=1[N+:27]([O-])=O)[CH2:7][C:8](=O)[C:9]([O:11][CH2:12][CH3:13])=[O:10])C.C(O)(=O)C>C1COCC1.C(Cl)Cl.[Cl-].[Na+].O.[Zn]>[CH2:12]([O:11][C:9]([C:8]1[O:30][C:5]2[C:4](=[O:3])[NH:27][C:16]3[C:17]([N:21]4[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]4)=[CH:18][CH:19]=[CH:20][C:15]=3[C:6]=2[CH:7]=1)=[O:10])[CH3:13]

参加物

7

反応物 2

HCID 176Acetic AcidHCID 597967863-(2-Nitro-3-piperidin-1-yl-phenyl)-2,5-dioxo-hexanedioic acid di ethyl ester

生成物 1

HCID 597967744-Oxo-6-piperidin-1-yl-4,5-dihydro-furo[2,3-c]quinoline-2-carboxylic acid ethyl ester

試薬・触媒・溶媒 4

HCID 23994Zinc触媒HCID 6344Dichloromethane溶媒HCID 8028Tetrahydrofuran溶媒HCID 57417360Sodium chloride; water溶媒

実験手順

A solution of 3-(2-nitro-3-piperidin-1-yl-phenyl)-2,5-dioxo-hexanedioic acid diethyl ester (iii) in THF is treated with acetic acid (“HOAc”) and is stirred at room temperature for 4 h. The reaction is treated with zinc dust (10 eq) and is stirred for an additional 2 h. The reaction is diluted with DCM, half saturated brine, and partitioned. The organic layer is washed with saturated aqueous NaHCO3, dried over MgSO4, filtered and concentrated. Chromatography gives 4-oxo-6-piperidin-1-yl-4,5-dihydro-furo[2,3-c]quinoline-2-carboxylic acid ethyl ester (iv).

後処理

  1. stirringis stirred for an additional 2 h
  2. custompartitioned
  3. washThe organic layer is washed with saturated aqueous NaHCO3
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-3f3d46e555544e16bb558b7e5d6bf3b5
出典データセット
uspto-grants-2008_09
特許番号
US07429603B2

反応ノート

読み込み中…