Methyl morpholine oxide → (3aR,6aS)-2-Oxo-3,3a,6,6a-tetrahydro-2H-cyclopenta[b]furan-5-carbaldehyde

Purified lactol 7 (800 mg, 4.15 mmol), was dissolved in CH2Cl2 (52 ml) and stirred at r.t. 4-Methylmorpholine N-oxide (729 mg, 6.23 mmol) and 4 Å molecular sieve (2.8 g) were added as solids and the reaction mixture was stirred at r.t. for 10 min. Tetrapropylammonium perruthenate (146 mg, 0.415 mmol) was added as a solid and the reaction was stirred at r.t. for 14 hours. The reaction mixture was filtered over Celite® and the solids were washed with CH2Cl2 (3×10 ml). The organic phase was concentrated to give the crude material as a black oil. The material was purified by column chromatography eluting with CH2Cl2/EtOAc (9:1), to give the lactone 54, (439 mg, 70%) as a white solid.

1. stirringthe reaction mixture was stirred at r.t. for 10 min
2. stirringthe reaction was stirred at r.t. for 14 hours
3. filtrationThe reaction mixture was filtered over Celite®
4. washthe solids were washed with CH2Cl2 (3×10 ml)
5. concentrationThe organic phase was concentrated
6. customto give the crude material as a black oil
7. customThe material was purified by column chromatography
8. washeluting with CH2Cl2/EtOAc (9:1)

ORD-Eintrag

ord-078a0d48e576464aaab0e2a9dad86840

Quelldatensatz

uspto-grants-2016_01

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09242954B2