Acetic Acid → (S)-2-benzylamino-3-phenyl-1-propanol

HRID 265691

반응식

HRID 265691 반응식
[NH2:1][C@H:2]([CH2:10][OH:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C(O)(=O)C.[CH:16](=O)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C([BH3-])#N.[Na+]>CO>[CH2:16]([NH:1][C@H:2]([CH2:10][OH:11])[CH2:3][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 240BenzaldehydeHCID 447213phenylalaninol, (S)-HCID 5003444Sodium cyanoborohydride

생성물 1

HCID 10514267(S)-2-benzylamino-3-phenyl-1-propanol수율 81%

시약·촉매·용매 1

HCID 887Methanol용매4회

반응 조건

온도
15 °C

실험 절차

L-Phenylalaninol (89.51 g, 0.592 moles) was dissolved in 375 mL of methanol under inert atmosphere, 35.52 g (0.592 moles) of glacial acetic acid and 50 mL of methanol was added followed by a solution of 62.83 g (0.592 moles) of benzaldehyde in 100 mL of methanol. The mixture was cooled to approximately 15° C. and a solution of 134.6 g(2.14 moles) of sodium cyanoborohydride in 700 mL of methanol was added in approximately 40 minutes, keeping the temperature between 15° C. and 25° C. The mixture was stirred at room temperature for 18 hours. The mixture was concentrated under reduced presssure and partitioned between 1 L of 2M ammonium hydroxide solution and 2 L of ether. The ether layer was washed with 1 L of 1M ammonium hydroxide solution, twice with 500 mL water, 500 mL of brine and dried over magnesium sulfate for 1 hour. The ether layer was filtered, concentrated under reduced pressure and the crude solid product was recrystallized from 110 mL of ethyl acetate and 1.3 L of hexane to give 115 g (81% yield) of N-benzyl-L-phenylalaninol as a white solid.

후처리

  1. additionwas added
  2. customthe temperature between 15° C. and 25° C
  3. concentrationThe mixture was concentrated under reduced presssure
  4. custompartitioned between 1 L of 2M ammonium hydroxide solution and 2 L of ether
  5. washThe ether layer was washed with 1 L of 1M ammonium hydroxide solution, twice with 500 mL water, 500 mL of brine
  6. dry with materialdried over magnesium sulfate for 1 hour
  7. filtrationThe ether layer was filtered
  8. concentrationconcentrated under reduced pressure
  9. customthe crude solid product was recrystallized from 110 mL of ethyl acetate and 1.3 L of hexane

출처 및 근거

ORD 기록
ord-095dccdb6e574a1db10a604b6fb9f1cc
출처 데이터셋
uspto-grants-1997_07
특허 번호
US05648511

연결된 노트

불러오는 중…