Reaktion #84723

Reaktionsgleichung

(4S)-4-methyl-3,7-dioxabicyclo[4.1.0]heptane

(R)-1-phenylethanamine

→

title compound

(3R,4S,6S)-6-methyl-4-((S)-1-phenylethylamino)tetrahydro-2H-pyran-3-ol

Lösungsmittel

isopropyl alcohol

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturAfter that, the solution was cooled to room temperature
2. 2
   Sonstigepurified by prep-HPLC

Vorschrift

A mixture of (4S)-4-methyl-3,7-dioxabicyclo[4.1.0]heptane (˜3 mL dichloromethane solution, 10 mmol) and (R)-1-phenylethanamine (2.4 g, 20 mmol) in isopropyl alcohol (20 mL) was stirred at 85° C. for 1 week. After that, the solution was cooled to room temperature and purified by prep-HPLC to get the title compound (more polar, 120 mg, 10% for 2 steps) as a yellow solid and a side product (less polar, 400 mg, 32% for 2 steps) as a white solid. MS (ES+) C14H21NO2 requires: 235, found: 236 [M+H]+.

Quelle