Ammonium Chloride → (3R,3aS,6aR)-hexahydrofuro(2,3-b)furan-3-ol

Into a mixed solution of methanol (25 ml) and 2-propanol (25 ml) was suspended (3aR, 6aR)-tetrahydrofuro[2,3-b]furan-3(2H)-one (10 g, 78.1 mmol), and sodium boron hydride (0.89 g, 23.4 mmol) was added divisionally to this at 0° C. and the mixture was stirred for 1.5 hours. After completion of the reaction, methanol (15 ml) and ammonium chloride (1.17 g, 21.9 mmol) were added and the mixture was stirred, then, the solvent was distilled off. To the concentrated residue was added 2-propanol (40 ml) and the mixture was concentrated again, and 2-propanol (40 ml) was added to this to cause dissolution. Insoluble materials were filtrated, then, concentration was performed to obtain a title compound in the form of yellow oil (9.87 g, yield 97.2%, (3R,3aS,6aR)-hexahydrofuro[2,3,b]furan-3-ol/(3S,3aS,6aR)-hexahydrofuro[2,3,b]furan-3-ol ratio=97.9/2.1).

1. additionwas added divisionally to this at 0° C.
2. additionwere added
3. stirringthe mixture was stirred
4. distillationthe solvent was distilled off
5. additionTo the concentrated residue was added 2-propanol (40 ml)
6. concentrationthe mixture was concentrated again
7. addition2-propanol (40 ml) was added to
8. dissolutiondissolution
9. filtrationInsoluble materials were filtrated
10. concentrationconcentration

ORD record

ord-fa2a3d19697c46a4a193f318914c7126

Source dataset

uspto-grants-2011_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07951977B2