Water → methyl 9-bromo-1-isobutyl-2,3,4,5-tetrahydro-1H-1-benzoazonin-6-carboxylate

HRID 402284ノート

反応式

HRID 402284 の反応式
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:13][CH2:12][CH2:11][CH2:10][CH2:9][C:8]([C:14]([O:16][CH3:17])=[O:15])=[CH:7][C:6]=2[CH:18]=1.O>ClCCCl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:13]([CH2:5][CH:6]([CH3:18])[CH3:7])[CH2:12][CH2:11][CH2:10][CH2:9][C:8]([C:14]([O:16][CH3:17])=[O:15])=[CH:7][C:6]=2[CH:18]=1

参加物

4

反応物 2

HCID 962WaterHCID 68649852methyl 9-bromo-2,3,4,5-tetrahydro-1H-1-benzoazonin-6-carboxylate

生成物 1

HCID 68650366methyl 9-bromo-1-isobutyl-2,3,4,5-tetrahydro-1H-1-benzoazonin-6-carboxylate収率 181.2%

試薬・触媒・溶媒 1

HCID 111,2-Dichloroethane溶媒

実験手順

To a solution of methyl 9-bromo-2,3,4,5-tetrahydro-1H-1-benzoazonin-6-carboxylate (2.0 g) in 1,2-dichloroethane (20 ml) were added isobutyl aldehyde (2.32 g) and triacetoxy sodium borohydride (4.11 g) and the mixture was stirred overnight. Water was added and the mixture was extracted with ethyl acetate, after which it was washed with aqueous saturated sodium bicarbonate solution and saturated brine, and dried with magnesium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1) to give methyl 9-bromo-1-isobutyl-2,3,4,5-tetrahydro-1H-1-benzoazonin-6-carboxylate (2.14 g) as a yellow oily material.

後処理

  1. extractionthe mixture was extracted with ethyl acetate
  2. washafter which it was washed with aqueous saturated sodium bicarbonate solution and saturated brine
  3. dry with materialdried with magnesium sulfate
  4. distillationThe solvent was distilled off under reduced pressure
  5. customthe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1)

出典と根拠

ORDレコード
ord-b9dab36547bd442d81c6148d98d570e0
出典データセット
uspto-grants-2014_06
特許番号
US08741943B2

反応ノート

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