Dimethyl Disulfide → HCID 10967752, compound

Temperature

-75 °C

(+)-(4aR)-(10bR)-4-methyl-8-bromo-10b-methyl-1,2,3,4,4a,5,6,10b-octahydrobenzo[f]quinolin-3-one (20.0 grams, 64.9 mmole, in 150 mL of tetrahydrofuran) was added to a freshly prepared solution of lithium diisopropylamide in 500 mL of tetrahydrofuran at -20° C. After standing 90 minutes in an ice bath, the resulting amide-enolate solution was cooled to -70° C. and added via cannula over 10 minutes to a freshly mixed solution of n-butyllithium (60.0 mL=2.54 M in hexane, 152 mmole, 2.34 equivalents) at -72 to -75° C. in 300 mL of tetrahydrofuran. The homogeneous solution was allowed to stir at approximately -75° C. for 45 minutes and quenched with dimethyldisulfide (11.0 mL, 123 mmole, 1.9 equiv) at approximately -75° C. After 30 minutes at -75° C., the mixture was treated with acetic acid (18 mL) and all volatiles removed under vacuum. The resulting white solid was treated with 300 mL of heptane-water (1:1, v/v) and the pH adjusted to 3 with 1N hydrogen sulfate. The biphasic mixture was filtered and the wet cake was washed with 1% aqueous sodium bicarbonate (2×50 mL portion) and water (200 mL). The material was dried at 50° C. under vacuum affording (+)-(4aR)-(10bR)-4-methyl-8-methylthio-10b-methyl-1,2,3,4,4a,5,6,10b-octahydrobenzo[f]quinolin-3-one (IR, NMR, MS). Calculated for C16H21NOS: C, 69.77; H, 7.69; N, 5.09. Found C, 69.70; H, 7.62; N, 5.06.

1. waitAfter 30 minutes at -75° C.
2. customall volatiles removed under vacuum
3. additionThe resulting white solid was treated with 300 mL of heptane-water (1:1
4. filtrationThe biphasic mixture was filtered
5. washthe wet cake was washed with 1% aqueous sodium bicarbonate (2×50 mL portion) and water (200 mL)
6. customThe material was dried at 50° C. under vacuum

ORD record

ord-c88ef4fefc4a49a2bc3f5db846c101b8

Source dataset

uspto-grants-2000_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06111110