Triphenylphosphine → 1-(t-Butoxycarbonyl)-4-(1-(2-fur-2-ylmethoxy-ethyl)-1h-benzimidazole-2-carbonyl)piperidine

HRID 379462Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 379462
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]([C:16]2[NH:20][C:19]3[CH:21]=[CH:22][CH:23]=[CH:24][C:18]=3[N:17]=2)=[O:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].O[CH2:26][CH2:27][O:28][CH2:29][C:30]1[O:31][CH:32]=[CH:33][CH:34]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1.CC(C)=O.ClCCl>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([C:14]([C:16]2[N:17]([CH2:26][CH2:27][O:28][CH2:29][C:30]3[O:31][CH:32]=[CH:33][CH:34]=3)[C:18]3[CH:24]=[CH:23][CH:22]=[CH:21][C:19]=3[N:20]=2)=[O:15])[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Komponenten

7

Edukt 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 10103270Fur-2-ylmethyl 2-hydroxyethyl etherHCID 183332351-(t-butoxycarbonyl)-4-(1H-benzimidazole-2-carbonyl)piperidine

Produkt 1

HCID 183334651-(t-Butoxycarbonyl)-4-(1-(2-fur-2-ylmethoxy-ethyl)-1h-benzimidazole-2-carbonyl)piperidine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 21584124Propan-2-one--dichloromethane (1/1)Lösungsmittel2×

Versuchsvorschrift

Combine ethyl 2-fur-2-ylmethoxyaceate (1.2 g, 6.5 mmol) and tetrahydrofuran (10 mL). Cool in an ice-bath. Add dropwise a solution of lithium aluminum hydride (8.0 mL, 1.0M in THF, 8.0 mmol). After 2 hours, add water (0.3 mL), add 15% sodium hydroxide solution (0.3 mL), and add water (0.9 mL). Stir vigorously. After 15 minutes, filter the reaction mixture and dry the filtrate over Na2SO4, filter, and concentrate in vacua to give a residue. Chromatograph the residue on silica gel eluting with 2% ethyl acetate/dichloromethane to give fur-2-ylmethyl 2-hydroxyethyl ether: Rf=0.22 (silica gel, 5% acetone/dichloromethane). Combine 1-(t-butoxycarbonyl)-4-(1H-benzimidazole-2-carbonyl)piperidine (1.71 g, 5.2 nmol), fur-2-ylmethyl 2-hydroxyethyl ether (0.74 g, 5.2 mmol), and triphenylphosphine (1.67 g, 6.4 mmol) in tetrahydrofuran (20 mL). Add diethyl azodicarboxylate (1.0 mL, 6.35 mmol). After 21 hours, evaporate the reaction mixture in vacuo to give a residue. Chromatograph the residue on silica gel eluting with 5% acetone/dichloromethane to give 1-(t-butoxycarbonyl)-4-(1-(2-fur-2-ylmethoxy-ethyl)-1H-benzimidazole-2-carbonyl)piperidine: Rf=0.30 (silica gel, 5% acetone/dichloromethane).

Aufarbeitung

  1. customevaporate the reaction mixture in vacuo
  2. customto give a residue

Quellen und Nachweise

ORD-Eintrag
ord-6ec932ba616941f28cdd6a0fea9ce53c
Quelldatensatz
uspto-grants-2001_10
Patentnummer
US06297259B1

Notizen zur Reaktion

Wird geladen…