Ammonia → 6-((tetrahydro-2H-pyran-2-yl)oxy)hexahydrofuro[3,2-b]furan-3-amine

To a solution of 6-((tetrahydro-2H-pyran-2-yl)oxy)tetrahydrofuro[3,2-b]furan-3(2H)-one (3.5 g, 15.3 mmol) in a solution of NH3 in MeOH (30 mL, 7 M) was added titanium isopropoxide (10.9 g, 38.3 mmol) at rt, and then the mixture was stirred at rt overnight. To the reaction mixture was added NaBH4 (1.16 g, 30.6 mmol) slowly at rt, and the mixture was stirred at rt for another 10 h and then quenched with H2O (50 mL). The resulting mixture was filtered and washed with EtOAc (50 mL). The filtrate was extracted with EtOAc (80 mL×3), and then the combined organic phases were washed with brine (200 mL), dried over anhydrous Na2SO4, then filtered and concentrated in vacuo to give product as crude oil (3.6 g, crude product).

1. stirringthe mixture was stirred at rt for another 10 h
2. customquenched with H2O (50 mL)
3. filtrationThe resulting mixture was filtered
4. washwashed with EtOAc (50 mL)
5. extractionThe filtrate was extracted with EtOAc (80 mL×3)
6. washthe combined organic phases were washed with brine (200 mL)
7. dry with materialdried over anhydrous Na2SO4
8. filtrationfiltered
9. concentrationconcentrated in vacuo
10. customto give product as crude oil (3.6 g, crude product)

ORD record

ord-4314607667a74f758479ad2fedc9df54

Source dataset

uspto-grants-2016_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09394281B2