Triethylamine → Benzyl 3-(3-hydroxypropyl)piperidine-1-carboxylate

HRID 2403820Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2403820
[C:1]1([CH2:7][O:8][C:9]([O:11]N2C(=O)CCC2=O)=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH:19]1[CH2:24][CH2:23][CH2:22][CH:21]([CH2:25][CH2:26][CH2:27][OH:28])[CH2:20]1.C(N(CC)CC)C>ClCCl>[OH:28][CH2:27][CH2:26][CH2:25][CH:21]1[CH2:22][CH2:23][CH2:24][N:19]([C:9]([O:8][CH2:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[O:11])[CH2:20]1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 83172Benzyl succinimido carbonateHCID 47124763-Piperidin-3-ylpropan-1-ol

Produkt 1

HCID 58306111Benzyl 3-(3-hydroxypropyl)piperidine-1-carboxylateAusbeute 87,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

1-({[(Phenylmethyl)oxy]carbonyl}oxy)-2,5-pyrrolidinedione (8.70 g), 34.9 mmol) was added portionwise to a stirred mixture of 3-(3-piperidinyl)-1-propanol (5.02 g, 35 mmol) and triethylamine (5 ml, 3.63 g, 35.9 mmol) in dichloromethane (100 ml) at room temperature. The resultant mixture was allowed to stand at room temperature for 18 hours. The reaction mixture was washed with saturated aqueous sodium hydrogen carbonate (100 ml). The organic phase was dried (MgSO4), filtered and evaporated. The sample was purified by chromatography on silica (100 g cartridge loaded in dichloromethane) using a gradient of 0-100% ethyl acetate-cyclohexane over 40 mins. The appropriate fractions were combined and evaporated in vacuo to give the title compound as a colourless liquid (8.45 g).

Aufarbeitung

  1. washThe reaction mixture was washed with saturated aqueous sodium hydrogen carbonate (100 ml)
  2. dry with materialThe organic phase was dried (MgSO4)
  3. filtrationfiltered
  4. customevaporated
  5. customThe sample was purified by chromatography on silica (100 g cartridge loaded in dichloromethane)
  6. customover 40 mins
  7. customevaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-3965ac8aeb924d249e92de8f6893a57e
Quelldatensatz
uspto-grants-2014_08
Patentnummer
US08802684B2

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