Piperidin-4-ol → 1-(Cyclopropylmethyl)piperidin-4-ol

HRID 1821982

Reaktionsgleichung

Reaktionsgleichung von HRID 1821982
Br[CH2:2][CH:3]1[CH2:5][CH2:4]1.[OH:6][CH:7]1[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]1>C1COCC1.C(OC(=O)C)C>[CH:5]1([CH2:4][N:10]2[CH2:11][CH2:12][CH:7]([OH:6])[CH2:8][CH2:9]2)[CH2:3][CH2:2]1

Komponenten

5

Edukt 2

HCID 79341Piperidin-4-olHCID 81503Bromomethylcyclopropane

Produkt 1

HCID 214287521-(Cyclopropylmethyl)piperidin-4-olAusbeute 47 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Add bromomethylcyclopropane (2.025 g, 15 mmol) to a solution of 4-hydroxypiperidine (3.035 g, 30 mmol) in THF (10 mL) and stir the mixture overnight. Dilute the mixture with ethylacetate, wash with saturated NaHCO3 solution, dry over Na2SO4, filter and concentrate to give a residue. Chromatography (silica gel, eluting with 8% 2M NH3-methanol in CH2Cl2) provides 1.087 g (47%) of the title compound: mass spectrum (ion spray): m/z=156.2 (M+1); 1H NMR (CDCl3, ppm): 3.60 (m, 1H), 2.81 (m, 2H), 2.16 (d, 1H), 2.10 (m, 3H), 1.84 (m, 2H), 1.53 (m, 3H), 0.79 (m, 1H), 0.44 (m, 2H), 0.00 (m, 2H).

Aufarbeitung

  1. washwash with saturated NaHCO3 solution
  2. dry with materialdry over Na2SO4
  3. filtrationfilter
  4. concentrationconcentrate
  5. customto give a residue
  6. washChromatography (silica gel, eluting with 8% 2M NH3-methanol in CH2Cl2)

Quellen und Nachweise

ORD-Eintrag
ord-477683910d6f4a09a72aa1c87f311dca
Quelldatensatz
uspto-grants-2009_10
Patentnummer
US07608629B2

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