Water → 6-(2,6-Dimethoxyphenyl)piperidin-2-one

HRID 594332ノート

反応式

HRID 594332 の反応式
[NH2:1][CH:2]([C:10]1[C:15]([O:16][CH3:17])=[CH:14][CH:13]=[CH:12][C:11]=1[O:18][CH3:19])[CH2:3][CH2:4][CH2:5][C:6](OC)=[O:7].C([O-])(O)=O.[Na+].O.CCOC(C)=O>C1COCC1>[CH3:19][O:18][C:11]1[CH:12]=[CH:13][CH:14]=[C:15]([O:16][CH3:17])[C:10]=1[CH:2]1[NH:1][C:6](=[O:7])[CH2:5][CH2:4][CH2:3]1

参加物

6

反応物 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 516892Sodium Bicarbonate2 回HCID 69082713Methyl 5-amino-5-(2,6-dimethoxyphenyl)pentanoate

生成物 1

HCID 690825266-(2,6-Dimethoxyphenyl)piperidin-2-one

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A yellow solution of the chlorhydrate salt of methyl 5-amino-5-(2,6-dimethoxyphenyl)pentanoate (14.96 mmol) in THF (92 ml) was treated with a solution of aq. sat. NaHCO3 (23.5 ml). The resulting heterogeneous mixture was further stirred at rt, under nitrogen, for 327 h. This reaction mixture was then treated with a solution of aq. sat. NaHCO3 (25 ml), water (50 ml), and AcOEt (200 ml). The layers were separated and the slightly yellow aq. layer was further extracted with AcOEt (50 ml). The mixed yellow organic layers were then dried over anh. MgSO4, filtered, and concentrated to dryness under reduced pressure. Purification by FC (DCM/MeOH=20/1) afforded 6-(2,6-dimethoxyphenyl)-piperidin-2-one as a beige solid. LC-MS (conditions B): tR=0.83 min.; [M+H]+: 236.49 g/mol.

後処理

  1. customThe layers were separated
  2. extractionthe slightly yellow aq. layer was further extracted with AcOEt (50 ml)
  3. dry with materialThe mixed yellow organic layers were then dried over anh. MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated to dryness under reduced pressure
  6. customPurification by FC (DCM/MeOH=20/1)

出典と根拠

ORDレコード
ord-87314d0c8f5e4ac9bb313a96384de3a0
出典データセット
uspto-grants-2016_01
特許番号
US09242970B2

反応ノート

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