Reaktion #84711

Reaktionsgleichung

4,4-dimethyl-3,7-dioxa-bicyclo[4.1.0]heptane

(R)-1-phenylethanamine

→

(4R,5R)-2,2-dimethyl-5-((R)-1-phenylethylamino)-tetrahydro-2H-pyran-4-ol

(4S,5S)-2,2-dimethyl-5-((R)-1-phenylethylamino)-tetrahydro-2H-pyran-4-ol

Lösungsmittel

isopropanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe reaction mixture was cooled to room temperature
2. 2
   Einengenconcentrated under reduced pressure
3. 3
   SonstigeThe residue was purified by silica gel chromatography (
4. 4
   Waschenelute

Vorschrift

A mixture of 4,4-dimethyl-3,7-dioxa-bicyclo[4.1.0]heptane (7.0 g, 54 mmol) and (R)-1-phenylethanamine (9.9 g, 82 mmol) in isopropanol (50 mL) was stirred at 80° C. for 6 days. The reaction mixture was cooled to room temperature and concentrated under reduced pressure. The residue was purified by silica gel chromatography (elute:petroleum ether:dichloromethane containing 1% ammonia-methanol (7 M), 10:1 to dichloromethane containing 1% ammonia/methanol (7 M) to afford (4R,5R)-2,2-dimethyl-5-((R)-1-phenylethylamino)-tetrahydro-2H-pyran-4-ol (6a) (more polar fraction, 1.5 g) and (4S,5S)-2,2-dimethyl-5-((R)-1-phenylethylamino)-tetrahydro-2H-pyran-4-ol (6b) (less polar fraction, 1.7 g) as a yellow oil. Note: The absolute configuration of the products was assigned randomly. MS (ES+) C15H23NO2 requires: 249, found: 250 [M+H]+. Mobile phase for TLC: ethyl acetate/dichloromethane=2/1.

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