Acetic Acid → Diethyl trans-1-benzyl-4-methoxypiperidin-3-ylphosphoramidate

HRID 2203710ノート

反応式

HRID 2203710 の反応式
[CH3:1][O:2][C@@H:3]1[CH2:8][CH2:7][NH:6][CH2:5][C@H:4]1[NH:9][P:10](=[O:17])([O:14][CH2:15][CH3:16])[O:11][CH2:12][CH3:13].[CH:18](=O)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(O)(=O)C.[BH3-]C#N.[Na+]>CO>[CH2:18]([N:6]1[CH2:7][CH2:8][C@@H:3]([O:2][CH3:1])[C@H:4]([NH:9][P:10](=[O:17])([O:14][CH2:15][CH3:16])[O:11][CH2:12][CH3:13])[CH2:5]1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

参加物

6

反応物 4

HCID 176Acetic AcidHCID 240BenzaldehydeHCID 5003444Sodium cyanoborohydrideHCID 67045828HCID 67045828、化合物

生成物 1

HCID 67045289Diethyl trans-1-benzyl-4-methoxypiperidin-3-ylphosphoramidate収率 98%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
0 °C

実験手順

A mixture of diethyl trans-4-methoxypiperidin-3-ylphosphoramidate (1.30 g, 4.88 mmol), benzaldehyde (0.74 mL, 7.32 mmol) and acetic acid (0.56 mL, 9.76 mmol) in methanol (20 mL) was stirred at 0° C. for 30 minutes. NaCNBH3 (0.46 g, 7.32 mmol) was added at 0° C. The resulting solution was warmed to room temperature and stirred at room temperature for 1 hour. The solvent was removed in vacuo and saturated sodium bicarbonate (20 mL) and ethyl acetate (30 mL) were added. The organic layer was separated, washed with brine, dried (sodium sulfate) and concentrated in vacuo to give diethyl trans-1-benzyl-4-methoxypiperidin-3-ylphosphoramidate (1.70 g, 98%), which was used directly in the next step without purification.

後処理

  1. temperatureThe resulting solution was warmed to room temperature
  2. stirringstirred at room temperature for 1 hour
  3. customThe solvent was removed in vacuo and saturated sodium bicarbonate (20 mL) and ethyl acetate (30 mL)
  4. additionwere added
  5. customThe organic layer was separated
  6. washwashed with brine
  7. dry with materialdried (sodium sulfate)
  8. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-31b86f754a214113bdda814f917f0ec3
出典データセット
uspto-grants-2016_06
特許番号
US09365568B2

反応ノート

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