Diisobutylaluminumhydride → 4-Oxo-6-piperidin-1-yl-4,5-dihydro-furo[2,3-c]quinoline-2-carbaldehyde

HRID 33475ノート

反応式

HRID 33475 の反応式
C([O:3][C:4]([C:6]1[O:25][C:9]2[C:10](=[O:24])[NH:11][C:12]3[C:13]([N:18]4[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]4)=[CH:14][CH:15]=[CH:16][C:17]=3[C:8]=2[CH:7]=1)=O)C.[H-].C([Al+]CC(C)C)C(C)C>C(Cl)Cl>[O:24]=[C:10]1[C:9]2[O:25][C:6]([CH:4]=[O:3])=[CH:7][C:8]=2[C:17]2[CH:16]=[CH:15][CH:14]=[C:13]([N:18]3[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]3)[C:12]=2[NH:11]1

参加物

4

反応物 2

HCID 21225700DiisobutylaluminumhydrideHCID 597967744-Oxo-6-piperidin-1-yl-4,5-dihydro-furo[2,3-c]quinoline-2-carboxylic acid ethyl ester

生成物 1

HCID 597967754-Oxo-6-piperidin-1-yl-4,5-dihydro-furo[2,3-c]quinoline-2-carbaldehyde

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A solution of 4-oxo-6-piperidin-1-yl-4,5-dihydro-furo[2,3-c]quinoline-2-carboxylic acid ethyl ester (iv) in DCM at 0° C. is treated with diisobutylaluminum hydride (“DIBAL-H”) and is allowed to warm to room temperature. The reaction is quenched with a saturated solution of sodium potassium tartrate and partitioned. The organic layer is dried over MgSO4, filtered and treated with manganese dioxide (“MnO2”). After stirring for 16 h at room temperature, the reaction is filtered and is concentrated to give 4-oxo-6-piperidin-1-yl-4,5-dihydro-furo[2,3-c]quinoline-2-carbaldehyde (v).

後処理

  1. customThe reaction is quenched with a saturated solution of sodium potassium tartrate
  2. custompartitioned
  3. dry with materialThe organic layer is dried over MgSO4
  4. filtrationfiltered
  5. additiontreated with manganese dioxide (“MnO2”)
  6. filtrationthe reaction is filtered
  7. concentrationis concentrated

出典と根拠

ORDレコード
ord-da03775be1b84d0aa2cf7170c8f040c1
出典データセット
uspto-grants-2008_09
特許番号
US07429603B2

反応ノート

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