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

HRID 1934381노트

반응식

HRID 1934381 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-e4a155b003454d9f9708f32ecab8adce
출처 데이터셋
uspto-grants-2002_05
특허 번호
US06384028B1

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