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

HRID 1034639노트

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HRID 1034639 반응식
[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

참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 240BenzaldehydeHCID 5003444Sodium cyanoborohydrideHCID 67045828HCID 67045828, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

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온도
0 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-79c68f02f8ab4967b80e672bc26de990
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08545897B2

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