Reaktion #41230

Reaktionsgleichung

product

(3aR,6aR)-5-Methyl-hexahydro-pyrrolo[3,4-b]pyrrole

1,4-dibromobenzene

racemic-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl

sodium tert-butoxide

→

title compound

(3aR,6aR)-1-(4-Bromo-phenyl)-5-methyl-octahydro-pyrrolo[3,4-b]pyrrole

Lösungsmittel

water

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe mixture was cooled to room temperature
2. 2
   Extraktionextracted with dichloromethane (5×)
3. 3
   TrocknenThe combined organics were dried over sodium sulfate
4. 4
   Filtrationfiltered
5. 5
   Einengenconcentrated
6. 6
   Sonstigepurified by chromatography (
7. 7
   Wascheneluting with a mixture of 5% methanol in dichloromethane)

Vorschrift

The product of Example 7B (2.30 g, 18.2 mmole), 1,4-dibromobenzene (5.16 g, 20.9 mmole), tris(dibenzylideneacetone)dipalladium (340 mg, 0.36 mmole), racemic-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (460 mg, 0.73 mmole) and sodium tert-butoxide (2.63 g, 27.3 mmole) were dissolved in 20 ml of toluene and heated to 70° C. under N2 for 16 hours. The mixture was cooled to room temperature, diluted with water and extracted with dichloromethane (5×). The combined organics were dried over sodium sulfate, filtered and concentrated and purified by chromatography (eluting with a mixture of 5% methanol in dichloromethane) to provide the title compound. 1H NMR (300 MHz, CDCl3) δ ppm 7.25-7.30 (m, 2H) 6.41-6.46 (m, 2H) 4.07(m, 1H) 3.47 (ddd, J=9.1, 7.7, 5.9 Hz, 1H) 3.19 (dt, J=8.9, 7.3 Hz, 1H) 2.95 (m, 1H) 2.68 (dd, J=9.0, 3.0 Hz, 1H) 2.55-2.60 (m, 3H) 2.32 (s, 3H) 2.13-2.22 (m, 1H) 1.88-1.98 (m, 1H). MS: (M+H)+=281/283.

Quelle