Acetic Acid → Benzyl 4-(1-(tert-butoxycarbonyl)piperidin-4-yl)piperazine-1-carboxylate

HRID 1631971ノート

反応式

HRID 1631971 の反応式
C([BH3-])#N.[Na+].O=[C:6]1[CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8][CH2:7]1.[CH2:19]1[NH:24][CH2:23][CH2:22][N:21]([C:25]([O:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[O:26])[CH2:20]1.C(O)(=O)C>CO>[C:15]([O:14][C:12]([N:9]1[CH2:10][CH2:11][CH:6]([N:24]2[CH2:19][CH2:20][N:21]([C:25]([O:27][CH2:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)=[O:26])[CH2:22][CH2:23]2)[CH2:7][CH2:8]1)=[O:13])([CH3:18])([CH3:17])[CH3:16]

参加物

6

反応物 4

HCID 176Acetic AcidHCID 643495Benzyl piperazine-1-carboxylateHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 5003444Sodium cyanoborohydride

生成物 1

HCID 18971584Benzyl 4-(1-(tert-butoxycarbonyl)piperidin-4-yl)piperazine-1-carboxylate

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

1.89 g (30.1 mmol) of sodium cyanoborohydride were added to a stirred solution of 3.00 g (15.1 mmol) of tert-butyl 4-oxo-1-piperidinecarboxylate and 3.48 g (15.8 mmol) of 1-Z-piperazine in methanol (60 ml) at room temperature. The pH of the solution was adjusted to about pH 7 by dropwise addition of acetic acid and was monitored during the course of the reaction. The reaction mixture was stirred at room temperature overnight and then concentrated in vacuo. The residue was mixed with water (60 ml) and extracted with dichloromethane (4×60 ml). The combined organic phases were washed with saturated NaCl solution, dried over magnesium sulfate and concentrated in vacuo. The residue was purified by chromatography on silica gel (mobile phase gradient 3-10% methanol in dichloromethane). Yield: 3.41 g (56%) of colorless oil

後処理

  1. customwas monitored during the course of the reaction
  2. concentrationconcentrated in vacuo
  3. additionThe residue was mixed with water (60 ml)
  4. extractionextracted with dichloromethane (4×60 ml)
  5. washThe combined organic phases were washed with saturated NaCl solution
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by chromatography on silica gel (mobile phase gradient 3-10% methanol in dichloromethane)

出典と根拠

ORDレコード
ord-fc7c907feea64a59b0cc329f31056fce
出典データセット
uspto-grants-2014_07
特許番号
US08791148B2

反応ノート

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