Acetic Acid → (1r)-1-(4-Piperidinyl)ethanol acetic acid salt

HRID 423656노트

반응식

HRID 423656 반응식
[N:1]1[CH:6]=[CH:5][C:4]([C@H:7]([OH:9])[CH3:8])=[CH:3][CH:2]=1.[CH3:10][C:11]([OH:13])=[O:12]>CO.O=[Pt]=O>[C:11]([OH:13])(=[O:12])[CH3:10].[NH:1]1[CH2:6][CH2:5][CH:4]([C@H:7]([OH:9])[CH3:8])[CH2:3][CH2:2]1

참가 물질

5

반응물 2

HCID 176Acetic AcidHCID 11804747(1R)-1-(pyridin-4-yl)ethan-1-ol

생성물 1

HCID 66673151(1r)-1-(4-Piperidinyl)ethanol acetic acid salt수율 79.5%

시약·촉매·용매 2

HCID 345198Adams' catalyst촉매HCID 887Methanol용매

실험 절차

(1R)-1-(4-pyridinyl)ethanol (61 g, 495 mmol, 96% ee) was dissolved in MeOH (1.5 L). The mixture was flushed with nitrogen and AcOH (40 mL, 0.7 mol) and PtO2 (15 g) were added. The mixture was stirred overnight under an atmosphere of hydrogen. The catalyst was removed by filtration and washed with MeOH (2×100 mL) and the filtrate was concentrated. The solid residue was mixed with EtOAc (500 mL) and stirred overnight. The resulting solid was collected by filtration, washed with EtOAc (3×100 mL) and dried under vacuum overnight to yield (1R)-1-(4-piperidinyl)ethanol acetic acid salt (74.5 g, 79% yield) as an off-white solid. 1H NMR (400 MHz, DMSO-d6): 3.30 (m, 1H), 3.03 (m, 2H), 2.55-2.50 (m, 2H), 1.76-1.69 (m, 1H), 1.69 (s, 3H), 1.51-1.44 (m, 1H), 1.27-1.16 (m, 3H), 0.96 (d, 3H, J=6.3 Hz).

후처리

  1. additionwere added
  2. customThe catalyst was removed by filtration
  3. washwashed with MeOH (2×100 mL)
  4. concentrationthe filtrate was concentrated
  5. additionThe solid residue was mixed with EtOAc (500 mL)
  6. stirringstirred overnight
  7. filtrationThe resulting solid was collected by filtration
  8. washwashed with EtOAc (3×100 mL)
  9. customdried under vacuum overnight

출처 및 근거

ORD 기록
ord-eb2aff83593c467f9fb5fff1380f184a
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08101634B2

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