Lithium tri-tert-butoxyaluminohydride → (3R,5R,8S,10S,13S,14S)-3-Hydroxy-10,13-dimethyl-3,4,5,6,7,8,10,12,13,14,15,16-dodecahydro-1H-cyclopenta[a]phenanthren-17(2H)-one

A THF solution of lithium tri-tert-butoxyaluminum hydride (1.0 M, 84.4 mL, 84.4 mmol) was added to a cold (−40° C.) solution of compound 1.2 (23.0 g, 80.4 mmol) in THF (230 mL) under an inert atmosphere. The resulting reaction mixture was stirred for 2 h. At this point the reaction was determined to be complete, as evidenced by TLC, and the reaction mixture was quenched by adding a mixture of 1N HCl (200 mL) and ethyl acetate (230 mL). The resulting two phase mixture was separated and the aqueous layer was extracted twice with ethyl acetate (2×100 mL). The organic phases were combined and washed sequentially with water (150 mL) and saturated brine solution (100 mL). The organic phase was then dried over Na2SO4 (75 g) and filtered. The filtrate was evaporated under vacuum to afford compound 1.3 (23.0 g) as an off-white solid. The above crude product was used “as is” in the next step without purification.

1. customThe resulting reaction mixture
2. customthe reaction mixture was quenched
3. additionby adding
4. additiona mixture of 1N HCl (200 mL) and ethyl acetate (230 mL)
5. customThe resulting two phase mixture was separated
6. extractionthe aqueous layer was extracted twice with ethyl acetate (2×100 mL)
7. washwashed sequentially with water (150 mL) and saturated brine solution (100 mL)
8. dry with materialThe organic phase was then dried over Na2SO4 (75 g)
9. filtrationfiltered
10. customThe filtrate was evaporated under vacuum

ORD record

ord-30aafdaee6b54b3493044d1b6c0012a6

Source dataset

uspto-grants-2013_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08367852B2