2-(2-Fluorophenyl)ethylamine → tert-butyl (4S,5R)-2-[2-(2-fluorophenyl)ethylamino]-4,5-diphenyl-4,5-dihydroimidazole-1-carboxylate

HRID 2053531

Reaktionsgleichung

Reaktionsgleichung von HRID 2053531
[C:1]1([C@H:7]2[C@@H:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[N:10]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[C:9](SC)=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[F:27][C:28]1[CH:36]=[CH:35][CH:34]=[CH:33][C:29]=1[CH2:30][CH2:31][NH2:32]>CO>[C:21]([O:20][C:18]([N:10]1[C@H:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C@H:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[N:8]=[C:9]1[NH:32][CH2:31][CH2:30][C:29]1[CH:33]=[CH:34][CH:35]=[CH:36][C:28]=1[F:27])=[O:19])([CH3:24])([CH3:23])[CH3:22]

Komponenten

4

Edukt 2

HCID 6433572-(2-Fluorophenyl)ethylamineHCID 86596320cis-4,5-Diphenyl-2-methylthio-4,5-dihydro-imidazole-1-carboxylic Acid, Tert-Butyl Ester

Produkt 1

HCID 68570675tert-butyl (4S,5R)-2-[2-(2-fluorophenyl)ethylamino]-4,5-diphenyl-4,5-dihydroimidazole-1-carboxylateAusbeute 43,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mixture of intermediate 59 (0.5 g, 1.36 mmol), 2-fluorophenethylamine (0.531 mL, 4.07 mmol) and MeOH (0.1 mL) is heated at 100° C. for 3 days. The reaction mixture is cooled to RT, and is purified by chromatography on silica gel; gradient elution with heptane:EtOAc (70:30-60:40) gives 0.27 g of the product 91. 1H NMR (CDCl3) δ 7.40-6.85 (m, 13H), 6.80-6.65 (m, 2H), 5.45-5.25 (m, 2H), 3.90-3.60 (m, 2H), 1.15 (s, 9H); MS: m/z 460 (M++1).

Aufarbeitung

  1. temperatureThe reaction mixture is cooled to RT
  2. customis purified by chromatography on silica gel
  3. washgradient elution with heptane:EtOAc (70:30-60:40)

Quellen und Nachweise

ORD-Eintrag
ord-a51d4890194d4f4bb726fd1f7be3b579
Quelldatensatz
uspto-grants-2008_02
Patentnummer
US07326792B2

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