Triphenylphosphine → 2-Aminocycloheptan-1-ol

HRID 1848019Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1848019
[N:1]([CH:4]1[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH:5]1[OH:11])=[N+]=[N-].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>C1COCC1.O>[NH2:1][CH:4]1[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH:5]1[OH:11]

Komponenten

5

Edukt 2

HCID 11776TriphenylphosphineHCID 145662602-Azidocycloheptan-1-ol

Produkt 1

HCID 128869132-Aminocycloheptan-1-olAusbeute 66,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a stirred mixture of (±)-2-azidocycloheptanol (190 mg, 1.2 mmol) in THF (1 mL) and H2O (100 μL) was added PPh3 (321 mg, 1.2 mmol). The mixture was stirred at rt for 15 h, then concentrated under reduced pressure. The residue was purified via silica gel flash chromatography eluting with 100:15:1, CH2Cl2:MeOH:TEA to afford (±)-2-aminocycloheptanol (103 mg, 50%) as a white solid. LCMS (ELSD) (ESI) m/z 130 (M+H)+.

Aufarbeitung

  1. concentrationconcentrated under reduced pressure
  2. customThe residue was purified via silica gel flash chromatography
  3. washeluting with 100:15:1, CH2Cl2

Quellen und Nachweise

ORD-Eintrag
ord-6ad0c534dc124358877ec05837199d7a
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08952058B2

Notizen zur Reaktion

Wird geladen…