Triphenylphosphine → tert-butyl N-{3-[1-(4-pyridyl)piperidin-4-yloxy]phenyl}carbamate

HRID 346668

Reaktionsgleichung

Reaktionsgleichung von HRID 346668
N(C(OCC)=O)=NC(OCC)=O.[N:13]1[CH:18]=[CH:17][C:16]([N:19]2[CH2:24][CH2:23][CH:22]([OH:25])[CH2:21][CH2:20]2)=[CH:15][CH:14]=1.[C:26]([O:30][C:31]([NH:33][C:34]1[CH:35]=[C:36](O)[CH:37]=[CH:38][CH:39]=1)=[O:32])([CH3:29])([CH3:28])[CH3:27].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[N:13]1[CH:18]=[CH:17][C:16]([N:19]2[CH2:24][CH2:23][CH:22]([O:25][C:38]3[CH:39]=[C:34]([NH:33][C:31](=[O:32])[O:30][C:26]([CH3:28])([CH3:27])[CH3:29])[CH:35]=[CH:36][CH:37]=3)[CH2:21][CH2:20]2)=[CH:15][CH:14]=1

Komponenten

6

Edukt 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 312485tert-butyl N-(3-hydroxyphenyl)carbamateHCID 234476191-(Pyridin-4-yl)piperidin-4-ol

Produkt 1

HCID 17915785tert-butyl N-{3-[1-(4-pyridyl)piperidin-4-yloxy]phenyl}carbamateAusbeute 66,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
4 °C

Versuchsvorschrift

Diethyl azodicarboxylate (3 ml) was added over 15 minutes to a stirred mixture of 1-(4-pyridyl)piperidin-4-ol (3.39 g), 3-(N-tert-butoxycarbonylamino)phenol (Chemical Abstracts, vol. 119, abstract 139113; PCT Patent Application WO 9306085; 3.98 g), triphenylphosphine (4.99 g) and THF (150 ml) which had been cooled to 4° C. The resultant mixture was stirred for 48 hours at ambient temperature. The solvent was evaporated and the residue was purified by column chromatography using a 9:1 mixture of methylene chloride and methanol as eluent. The resultant foam was crystallised from diethyl ether to give tert-butyl N-{3-[1-(4-pyridyl)piperidin-4-yloxy]phenyl}carbamate (4.65 g), m.p. 165-166° C.

Aufarbeitung

  1. customThe solvent was evaporated
  2. customthe residue was purified by column chromatography
  3. additiona 9:1 mixture of methylene chloride and methanol as eluent
  4. customThe resultant foam was crystallised from diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-824e5e37bf714049a6b5762aa95f07f4
Quelldatensatz
uspto-grants-2007_02
Patentnummer
US07173025B1

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