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

HRID 1711222노트

반응식

HRID 1711222 반응식
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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-82f02b1b6217423d817ef409d1ea8ae7
출처 데이터셋
uspto-grants-2010_09
특허 번호
US07790724B2

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