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

HRID 423656ノート

反応式

HRID 423656 の反応式
[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

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 345198Adams' catalyst触媒HCID 887Methanol溶媒

実験手順

(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).

後処理

  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

出典と根拠

ORDレコード
ord-eb2aff83593c467f9fb5fff1380f184a
出典データセット
uspto-grants-2012_01
特許番号
US08101634B2

反応ノート

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