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Triphenylphosphine → 3-(7-bromo-1,2,3,4-tetrahydro-naphthalen-1-yl)-3H-imidazole-4-carboxylic acid isopropyl ester

HRID 2089471
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Reaktionsgleichung

Reaktionsgleichung von HRID 2089471
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][CH2:8][CH:9]2O)=[CH:4][CH:3]=1.[NH:13]1[CH:17]=[C:16]([C:18]([O:20][CH:21]([CH3:23])[CH3:22])=[O:19])[N:15]=[CH:14]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC)=O)=NC(OC)=O>C1COCC1>[CH:21]([O:20][C:18]([C:16]1[N:15]([CH:9]2[C:10]3[C:5](=[CH:4][CH:3]=[C:2]([Br:1])[CH:11]=3)[CH2:6][CH2:7][CH2:8]2)[CH:14]=[N:13][CH:17]=1)=[O:19])([CH3:23])[CH3:22]
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Komponenten

6

Edukt 4

HCID 11776TriphenylphosphineHCID 351621Azodicarboxylic acid dimethyl esterHCID 126949197-Bromo-1,2,3,4-tetrahydronaphthalen-1-olHCID 178459416HCID 178459416, Verbindung

Produkt 1

HCID 591994563-(7-bromo-1,2,3,4-tetrahydro-naphthalen-1-yl)-3H-imidazole-4-carboxylic acid isopropyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a suspension of 7-bromo-1,2,3,4-tetrahydro-naphthalen-1-ol (2.5 g, 11.0 mmol) and isopropyl 4-imidazolecarboxylate (1.18 g, 7.66 mmol), which can be prepared as described in Example 1, (2.33 g, 10.98 mmol) in THF (20 mL) at 0° C. is added triphenylphosphine and dimethyl azodicarboxylate (40% wt. in toluene, 4.01 g, 10.98 mmol). After 10 min, the cooling bath is removed and after another 30 min, water is added and the mixture is extracted twice with ethyl acetate. The organic layers are dried over magnesium sulfate, filtered, and concentrated. The resulting residue is purified by silica gel chromatography (elution with hexanes-ethyl acetate mixtures) to give 3-(7-bromo-1,2,3,4-tetrahydro-naphthalen-1-yl)-3H-imidazole-4-carboxylic acid isopropyl ester; MS: (ESI) m/z 363.02, 365.02 (M+H)+; 1H NMR (400 MHz, MeOD) δ ppm 1.42 (d, J=6.1 Hz, 3 H), 1.44 (d, J=6.3 Hz, 3 H), 1.73-1.84 (m, 1 H), 1.89-1.98 (m, 1 H), 2.26-2.40 (m, 2 H), 2.82-2.91 (m, 1 H), 3.00 (dt, J=17.2, 5.6 Hz, 1 H), 5.27-5.37 (m, 1 H), 6.50 (t, J=5.3 Hz, 1 H), 7.26 (d, J=8.3 Hz, 1 H), 7.32 (d, J=2.1 Hz, 1 H), 7.51 (dd, J=8.3, 2.1 Hz, 1 H), 8.23 (d, J=1.5 Hz, 1 H), 8.50 (d, J=1.0 Hz, 1 H).

Aufarbeitung

  1. customcan be prepared
  2. customthe cooling bath is removed and after another 30 min
  3. additionwater is added
  4. extractionthe mixture is extracted twice with ethyl acetate
  5. dry with materialThe organic layers are dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe resulting residue is purified by silica gel chromatography (elution with hexanes-ethyl acetate mixtures)

Quellen und Nachweise

ORD-Eintrag
ord-889f6a26606e43ca981a5dcd4273e16b
Quelldatensatz
uspto-grants-2013_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08436035B2

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