Sulfuric Acid → HCID 10960808, compound

Temperature

0 °C

To a 1 M solution of lithium aluminum hydride in ethyl ether (91.5 ml) was added dropwise at 0° C. a 7.2 M solution of sulfuric acid in THF (6.4 ml) and the mixture was stirred at 0° C. for 1 h. To the mixture at 0° C. was added 8 (10.9 g) in THF (75 ml). The reaction mixture was allowed to warm to RT and stirred for 3.5 h at RT at which point it was cooled back to 0° C. and a 30% (v/v) solution of H2O in THF was added dropwise. A 1 N solution of NaOH (15 ml) was added. The reaction mixture was filtered through a sintered glass funnel to remove the aluminum oxides. The filtrate was transferred to a separatory funnel and partitioned between water and ethyl ether. The aqueous layer was extracted three times with ether. The organic phase was dried (Na2SO4) and concentrated. The resulting oil was taken up in THF (175 ml). To the THF solution was added t-butanol (60 ml), N-methyl-morpholine-N-oxide (10.7 g) and osmium tetraoxide (2.5 wt % in t-butanol, 7.6 ml). The reaction mixture was stirred for 18 h at RT. The reaction mixture was transferred to a separatory funnel and partitioned between brine and ethyl acetate. The aqueous layer was extracted three times with ethyl acetate. The organic layer was dried, concentrated and the residue applied to a silica gel column. The product was eluted with 10% ethyl acetate/petroleum ether giving 9 (10.92 g).

1. temperatureto warm to RT
2. stirringstirred for 3.5 h at RT at which point it
3. temperaturewas cooled back to 0° C.
4. filtrationThe reaction mixture was filtered through a sintered glass funnel
5. customto remove the aluminum oxides
6. customThe filtrate was transferred to a separatory funnel
7. custompartitioned between water and ethyl ether
8. extractionThe aqueous layer was extracted three times with ether
9. dry with materialThe organic phase was dried (Na2SO4)
10. concentrationconcentrated
11. additionTo the THF solution was added t-butanol (60 ml), N-methyl-morpholine-N-oxide (10.7 g) and osmium tetraoxide (2.5 wt % in t-butanol, 7.6 ml)
12. stirringThe reaction mixture was stirred for 18 h at RT
13. customThe reaction mixture was transferred to a separatory funnel
14. custompartitioned between brine and ethyl acetate
15. extractionThe aqueous layer was extracted three times with ethyl acetate
16. customThe organic layer was dried
17. concentrationconcentrated
18. washThe product was eluted with 10% ethyl acetate/petroleum ether giving 9 (10.92 g)

ORD record

ord-3635046cf2684af4b345469aacf128b6

Source dataset

uspto-grants-2002_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06465451B1