Ethanol → (R)-1-[3-(1-tert-butoxycarbonyl-4-piperidyl)-(E)-acryloyl]-3-piperidinecarboxylic acid

HRID 1934381ノート

反応式

HRID 1934381 の反応式
[Li+].[OH-].[C:3]([O:7][C:8]([N:10]1[CH2:15][CH2:14][CH:13](/[CH:16]=[CH:17]/[C:18]([N:20]2[CH2:25][CH2:24][CH2:23][C@@H:22]([C:26]([O:28]CC)=[O:27])[CH2:21]2)=[O:19])[CH2:12][CH2:11]1)=[O:9])([CH3:6])([CH3:5])[CH3:4].CCO>O.O1CCCC1>[C:3]([O:7][C:8]([N:10]1[CH2:11][CH2:12][CH:13](/[CH:16]=[CH:17]/[C:18]([N:20]2[CH2:25][CH2:24][CH2:23][C@@H:22]([C:26]([OH:28])=[O:27])[CH2:21]2)=[O:19])[CH2:14][CH2:15]1)=[O:9])([CH3:6])([CH3:4])[CH3:5]

参加物

6

反応物 3

HCID 702EthanolHCID 3939Lithium HydroxideHCID 86758023ethyl (R)-1-[3-(1-tert-butoxycarbonyl-4-piperidyl)-(E)-acryloyl]-3-piperidinecarboxylate

生成物 1

HCID 69817990(R)-1-[3-(1-tert-butoxycarbonyl-4-piperidyl)-(E)-acryloyl]-3-piperidinecarboxylic acid収率 74.1%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of LiOH (0.32 g) in H2O (20 ml) was added to a solution of ethyl (R)-1-[3-(1-tert-butoxycarbonyl-4-piperidyl)-(E)-acryloyl]-3-piperidinecarboxylate (4.46 g) in tetrahydrofuran (20 ml)-EtOH (20 ml) at 0° C. The reaction mixture was stirred for 3 hours at the same condition, and the solvent was evaporated in vacuo. The residue was resolved in ethyl acetate-water, and acidified with 10% aq. KHSO4. The whole was washed with water, brine, dried over MgSO4, and evaporated in vacuo, subsequently. The residue was recrystallized from diethyl ether to give (R)-1-[3-(1-tert-butoxycarbonyl-4-piperidyl)-(E)-acryloyl]-3-piperidinecarboxylic acid as a white solid (3.07 g).

後処理

  1. customthe solvent was evaporated in vacuo
  2. washThe whole was washed with water, brine
  3. dry with materialdried over MgSO4
  4. customevaporated in vacuo
  5. customThe residue was recrystallized from diethyl ether

出典と根拠

ORDレコード
ord-e4a155b003454d9f9708f32ecab8adce
出典データセット
uspto-grants-2002_05
特許番号
US06384028B1

反応ノート

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