Triphenylphosphine → 1-t-Butoxycarbonyl-2-{2-[2-(4-phenylbutyl)phenoxy]ethyl}piperidine

HRID 743237Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 743237
[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[OH:17])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:18]([O:22][C:23]([N:25]1[CH2:30][CH2:29][CH2:28][CH2:27][CH:26]1[CH2:31][CH2:32]O)=[O:24])([CH3:21])([CH3:20])[CH3:19].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C(Cl)Cl>[C:18]([O:22][C:23]([N:25]1[CH2:30][CH2:29][CH2:28][CH2:27][CH:26]1[CH2:31][CH2:32][O:17][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=1[CH2:10][CH2:9][CH2:8][CH2:7][C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)=[O:24])([CH3:21])([CH3:20])[CH3:19]

Komponenten

6

Edukt 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 5103438Tert-butyl 2-(2-hydroxyethyl)piperidine-1-carboxylateHCID 125964892-(4-Phenylbutyl)phenol

Produkt 1

HCID 108367361-t-Butoxycarbonyl-2-{2-[2-(4-phenylbutyl)phenoxy]ethyl}piperidineAusbeute 34,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Following a procedure similar to that described in Example 5(a), 1.69 g of 2-(4-phenylbutyl)phenol (prepared as described in Preparation 3), 1.72 g of 1-t-butoxycarbonyl-2-(2-hydroxyethyl)piperidine, 5.9 g of triphenylphosphine and 3.92 g of diethyl azodicarboxylate were reacted in 75 ml of methylene chloride. The crude oily product, extracted as described in Example 5(a), was purified by column chromatography through silica gel, using a 5:1 by volume mixture of hexane and ethyl acetate as the eluent, to give 1.13 g (yield 34%) of the title compound as an oil.

Aufarbeitung

  1. extractionThe crude oily product, extracted
  2. customwas purified by column chromatography through silica gel
  3. additionby volume mixture of hexane and ethyl acetate as the eluent

Quellen und Nachweise

ORD-Eintrag
ord-4079b2cba14c4eff88d617befb2759a7
Quelldatensatz
uspto-grants-1996_09
Patentnummer
US05556864

Notizen zur Reaktion

Wird geladen…