Reaktion #69434

Reaktionsgleichung

sodium bisulfite

cyclopent-3-en-1-ylmethyl 4-nitrobenzoate

4-methylmorpholine N-oxide

butanol

acetone

→

title compound

(3,4-dihydroxycyclopentyl)methyl 4-nitrobenzoate

Lösungsmittel

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGthe solution was stirred for 30 min
2. 2
   ExtraktionThe solution was then extracted with ethyl acetate
3. 3
   Trocknenthe combined organic layers were dried (magnesium sulfate)
4. 4
   Filtrationfiltered
5. 5
   Einengenconcentrated in vacua
6. 6
   SonstigeThe residue was purified by silica gel chromatography (Biotage 65i)
7. 7
   Wascheneluting with 0-100% ethyl acetate/hexanes

Vorschrift

Osmium tetroxide (235 μL, 0.75 mmol) was added to a solution of cyclopent-3-en-1-ylmethyl 4-nitrobenzoate (3.70 g, 15.0 mmol) and 4-methylmorpholine N-oxide (1.93 g, 16.5 mmol) in tent-butanol (6.7 mL)/water (40 mL)/acetone (13.3 mL). The solution was stirred at room temperature for 16 hours. Aqueous sodium bisulfite solution was added, and the solution was stirred for 30 min. The solution was then extracted with ethyl acetate, and the combined organic layers were dried (magnesium sulfate), filtered, and concentrated in vacua. The residue was purified by silica gel chromatography (Biotage 65i), eluting with 0-100% ethyl acetate/hexanes to give the title compound as a colorless oil. 1H NMR (500 MHz, CHCl3) δ 1.67-1.75 (m, 2H), 1.95-2.00 (m, 2H), 2.80-2.85 (m, 1H), 4.21 (quintet, J=4.1 Hz, 2H), 4.26 (d, J=6.7 Hz, 2H), 8.19 (d, J=8.7 Hz, 2H), 8.29 (d, J=8.7 Hz, 2H).

Quelle