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 2381092ノート

反応式

HRID 2381092 の反応式
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

参加物

4

反応物 1

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 887Methanol溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-59321207f50a42e6bb97ef341b4e98a8
出典データセット
uspto-grants-2012_09
特許番号
US08258140B2

反応ノート

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