Acetic Acid → HCID 11738489, compound

To a solution of 2,3,4,9-tetrahydro-1H-carbazol-1-one (0.1 g, 0.52 mmol) in dichloroethane (5 mL) was added sodium triacetoxyborohydride (0.17 g, 0.80 mmol), acetic acid (0.046 mL, 0.80 mmol) and benzyl amine (0.087 mL, 0.80 mmol). The mixture was stirred at room temperature for 16 hours. The reaction was quenched by adding saturated NaHCO3 (5 mL) and EtOAc (5 mL) and stirred for 30 minutes. The layers were separated, the aqueous layer extracted with EtOAc (2×5 mL), the organic layers combined, dried over Na2SO4, filtered and evaporated. Purification was accomplished by silica gel chromatography with hexanes/ethyl acetate as the eluant to afford yellowish oil. The compound was dissolved in diethyl ether and a solution of HCl in diethyl ethyl ether was added to yield a white precipitate was upon evaporation. Recrystallization from methanol/diethyl ether afforded a white solid (42 mg, 35%). 1H-NMR (DMSO-ds): δ 11.2 (s, 1H), 9.70 (s, 1H), 9.58 (s, 1H), 7.64 (d, 2H), 7.43 (m, 5H), 7.14 (t, 1H), 7.02 (t, 1H), 4.67 (s, 1H), 4.29 (s, 2H), 2.71 (m, 2H), 2.22 (m, 2H), 2.08 (m, 1H), 1.82(m, 1H); 13C-NMR (CDCl3): δ 140.7, 136.2, 135.7, 128.5, 128.1, 127.5, 127.1, 121.5, 119.0, 118.3, 111.2, 110.8, 51.9, 50.4, 30.5, 21.8, 21.0; MS m/z 277 (M).

1. customThe reaction was quenched
2. additionby adding saturated NaHCO3 (5 mL) and EtOAc (5 mL)
3. stirringstirred for 30 minutes
4. customThe layers were separated
5. extractionthe aqueous layer extracted with EtOAc (2×5 mL)
6. dry with materialdried over Na2SO4
7. filtrationfiltered
8. customevaporated
9. customPurification
10. customto afford yellowish oil
11. customto yield a white precipitate
12. customwas upon evaporation
13. customRecrystallization from methanol/diethyl ether

ORD record

ord-6c78d6f7ef344465a6b2037ecf4fa359

Source dataset

uspto-grants-2009_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07622494B2