(1R,3s,5S)-methyl 6-oxabicyclo[3.1.0]hexane-3-carboxylate → Methyl (1S,3S)-3-hydroxycyclopentanecarboxylate
Reaktionsgleichung
[C@@H:1]12[O:6][C@@H:5]1[CH2:4][CH:3]([C:7]([O:9][CH3:10])=[O:8])[CH2:2]2>CC(OC)(C)C>[OH:6][C@H:1]1[CH2:5][CH2:4][C@H:3]([C:7]([O:9][CH3:10])=[O:8])[CH2:2]1Komponenten
3
Edukt 1
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
A solution of methyl (1S,5R)-6-oxabicyclo[3.1.0]hexane-3-carboxylate (8 g, 56.3 mmol) in MTBE (100 ml) was hydrogenated at 3 atm on Parr shaker for 12 hrs. Filtered through celite evaporated followed by chromatagraphy on a 50 g silica gel Biotage Snap cartridge with 10-50% 6:3:1 Hexane-MTBE-MeCN/Hexane to give title compound. 1H NMR (500 MHz, CDCl3) δ 1.63-1.74 (m, 3H), δ 1.78 (s, br, 1H), δ 1.82-2.07 (m, 4H), δ 2.11-2.19 (m, 1H), δ 3.09 (m, 1H), δ 3.70 (s, 3H), δ 4.48 (m, 1H)
Aufarbeitung
- filtrationFiltered through celite
- customevaporated
Quellen und Nachweise
- ORD-Eintrag
- ord-322b1f56ae174129abd8188c9fa41142
- Quelldatensatz
- uspto-grants-2012_02
- Patentnummer
- US08119806B2
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