Water → 5-Methoxy-1-methyl-4-[4-nitro-3-(propan-2-yloxy)phenyl]-1,2,3,6-tetrahydropyridine

HRID 518800ノート

反応式

HRID 518800 の反応式
[BH4-].[Na+].[I-].[CH3:4][O:5][C:6]1[CH:7]=[N+:8]([CH3:25])[CH:9]=[CH:10][C:11]=1[C:12]1[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[C:14]([O:21][CH:22]([CH3:24])[CH3:23])[CH:13]=1.O.C(OCC)(=O)C>C(O)C>[CH3:4][O:5][C:6]1[CH2:7][N:8]([CH3:25])[CH2:9][CH2:10][C:11]=1[C:12]1[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[C:14]([O:21][CH:22]([CH3:24])[CH3:23])[CH:13]=1

参加物

6

反応物 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 4311764Sodium borohydrideHCID 866979693-Methoxy-1-methyl-4-[4-nitro-3-(propan-2-yloxy)phenyl]pyridinium iodide

生成物 1

HCID 866979715-Methoxy-1-methyl-4-[4-nitro-3-(propan-2-yloxy)phenyl]-1,2,3,6-tetrahydropyridine収率 76.7%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

672 mg of NaBH4 are added, in portions, to a suspension of 5.09 g of 3-methoxy-1-methyl-4-[4-nitro-3-(propan-2-yloxy)phenyl]pyridinium iodide in 90 ml of ethanol brought to 5° C. the reaction medium is stirred for 30 minutes at ambient temperature. 50 ml of water and 100 ml of ethyl acetate are added. The two phases are separated, and the aqueous phase is washed with twice 50 ml of ethyl acetate. The combined organic phases are dried over magnesium sulfate, filtered and evaporated. Purification is carried out by flash chromatography on silica gel (40-63 μm), elution being carried out with a mixture of dichloromethane and acetone (95/5 to 80/20). 2.78 g of 5-methoxy-1-methyl-4-[4-nitro-3-(propan-2-yloxy)phenyl]-1,2,3,6-tetrahydropyridine are obtained in the form of a brown oil.

後処理

  1. custombrought to 5° C.
  2. customThe two phases are separated
  3. washthe aqueous phase is washed with twice 50 ml of ethyl acetate
  4. dry with materialThe combined organic phases are dried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customPurification
  8. washis carried out by flash chromatography on silica gel (40-63 μm), elution
  9. additionbeing carried out with a mixture of dichloromethane and acetone (95/5 to 80/20)

出典と根拠

ORDレコード
ord-4addf5e4ac614f7baa910f06935a035b
出典データセット
uspto-grants-2015_08
特許番号
US09115140B2

反応ノート

読み込み中…