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

HRID 1044881Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1044881
[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-85a5e0b4479b44e18af9ea65d0986d6b
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08563717B2

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