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1-Phenethylamine, (+)- → rel-1-(1,1-Dimethylethyl) 3-methyl (3R,5S)-1,3,5-piperidinetricarboxylate

HRID 1259874
ノート
印刷プレビュー

反応式

HRID 1259874 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH:12]([C:14]([O:16][CH3:17])=[O:15])[CH2:11][CH:10]([C:18]([OH:20])=[O:19])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1([C@H](N)C)C=CC=CC=1>C(O)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][C@H:12]([C:14]([O:16][CH3:17])=[O:15])[CH2:11][C@H:10]([C:18]([OH:20])=[O:19])[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

4

反応物 2

HCID 6431891-Phenethylamine, (+)-HCID 232911511-((Tert-butoxy)carbonyl)-5-(methoxycarbonyl)piperidine-3-carboxylic acid

生成物 1

HCID 11358159rel-1-(1,1-Dimethylethyl) 3-methyl (3R,5S)-1,3,5-piperidinetricarboxylate収率 14.9%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
70 °C

実験手順

A mixture of (3RS,5SR)-1-(tert-butoxycarbonyl)-5-(methoxycarbonyl)piperidine-3-carboxylic acid (6.16 g), (R)-(+)-1-phenylethylamine (2.60 g) and ethanol (24 ml) was dissolved by heating to 70° C., and recrystallized. The precipitated crystals were collected by filtration, dissolved in ethanol (7 ml) again and recrystallized. The precipitated crystals were collected by filtration, the obtained crystals were suspended in water, acidified by adding saturated aqueous potassium hydrogen sulfate solution, and the mixture was extracted 3 times with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to give the object product (915 mg) as a powder.

後処理

  1. dissolutionwas dissolved
  2. customrecrystallized
  3. filtrationThe precipitated crystals were collected by filtration
  4. dissolutiondissolved in ethanol (7 ml) again
  5. customrecrystallized
  6. filtrationThe precipitated crystals were collected by filtration
  7. additionby adding saturated aqueous potassium hydrogen sulfate solution
  8. extractionthe mixture was extracted 3 times with ethyl acetate
  9. washThe extract was washed with saturated brine
  10. dry with materialdried over anhydrous magnesium sulfate
  11. customThe solvent was evaporated under reduced pressure

出典と根拠

ORDレコード
ord-f7cc1ce8b7994004bae695145ad89763
出典データセット
uspto-grants-2013_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08466282B2

反応ノート

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