Tert-butyl 4-[2-[4-(1-(benzyloxycarbonyl)-1,2,3,6-tetrahydropyridin-4-yl)phenoxy]ethyl]piperazine-1-carboxylate → Tert-butyl 4-[2-[4-(piperidin-4-yl)phenoxy]ethyl]piperazine-1-carboxylate

HRID 2381092노트

반응식

HRID 2381092 반응식
C(OC([N:11]1[CH2:16][CH:15]=[C:14]([C:17]2[CH:38]=[CH:37][C:20]([O:21][CH2:22][CH2:23][N:24]3[CH2:29][CH2:28][N:27]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:26][CH2:25]3)=[CH:19][CH:18]=2)[CH2:13][CH2:12]1)=O)C1C=CC=CC=1>[Pd].CO>[NH:11]1[CH2:16][CH2:15][CH:14]([C:17]2[CH:38]=[CH:37][C:20]([O:21][CH2:22][CH2:23][N:24]3[CH2:29][CH2:28][N:27]([C:30]([O:32][C:33]([CH3:34])([CH3:36])[CH3:35])=[O:31])[CH2:26][CH2:25]3)=[CH:19][CH:18]=2)[CH2:13][CH2:12]1

참가 물질

4

반응물 1

HCID 66788330Tert-butyl 4-[2-[4-(1-(benzyloxycarbonyl)-1,2,3,6-tetrahydropyridin-4-yl)phenoxy]ethyl]piperazine-1-carboxylate

생성물 1

HCID 66788225Tert-butyl 4-[2-[4-(piperidin-4-yl)phenoxy]ethyl]piperazine-1-carboxylate수율 90.4%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 887Methanol용매

실험 절차

tert-Butyl 4-[2-[4-(1-(benzyloxycarbonyl)-1,2,3,6-tetrahydropyridin-4-yl)phenoxy]ethyl]piperazine-1-carboxylate (66% pure by weight) (34.62 g, 43.80 mmol) and 5% palladium on carbon (50% wet) (4.47 g, 1.05 mmol) in MeOH (250 mL) were stirred under an atmosphere of hydrogen at 5 bar and 60° C. for 4 hours. The catalyst was removed by filtration and the solvents evaporated to give crude product. The crude product was purified by flash silica chromatography, eluting with 60% EtOAc in isohexane then 15% 2M ammonia/MeOH in DCM. Pure fractions were evaporated to dryness to afford tert-butyl 4-[2-[4-(piperidin-4-yl)phenoxy]ethyl]piperazine-1-carboxylate (15.42 g, 90%) as a solid.

후처리

  1. customThe catalyst was removed by filtration
  2. customthe solvents evaporated
  3. customto give crude product
  4. customThe crude product was purified by flash silica chromatography
  5. washeluting with 60% EtOAc in isohexane
  6. customPure fractions were evaporated to dryness

출처 및 근거

ORD 기록
ord-59321207f50a42e6bb97ef341b4e98a8
출처 데이터셋
uspto-grants-2012_09
특허 번호
US08258140B2

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