HCID 19759896, compound → HCID 19759897, compound

Temperature

10 °C

Borane-dimethylsulfide complex (11.12 mL, 10M) was added to a stirred solution of 2,3-dihydro-2-methylthieno[2,3-b]thiophene-2-carboxamide-1,1-dioxide (2.57 g, 11.12 mmol) in THF (75 mL) at room temperature. The reaction mixture was refluxed under a nitrogen atmosphere for 1.5 h and then cooled in an ice bath to 10° C. and slowly quenched with 6N HCl. After gas evolution ceased, the acidic solution was refluxed for 2 h. The reaction mixture was cooled to room temperature and extracted twice with ether. The aqueous phase was made alkaline with aqueous NaOH and extracted with ethyl acetate (5×300 mL). The combined ethyl acetate extracts were washed with saturated brine and then dried over MgSO4. The solution was filtered and the solvent removed in vacuo to give 2-aminomethyl-2,3-dihydro-2-methylthieno[2,3-b]thiophene-1,1-dioxide as an oil (2.2 g, 91%). 1H NMR (300 MHz,DMSO-d6) 1.40(s,3H), 2.85-3.00(m,3H), 3.30(d,1H), 7.05(s,1H), 8.05(s,1H).

1. temperatureThe reaction mixture was refluxed under a nitrogen atmosphere for 1.5 h
2. customslowly quenched with 6N HCl
3. temperaturethe acidic solution was refluxed for 2 h
4. temperatureThe reaction mixture was cooled to room temperature
5. extractionextracted twice with ether
6. extractionextracted with ethyl acetate (5×300 mL)
7. washThe combined ethyl acetate extracts were washed with saturated brine
8. dry with materialdried over MgSO4
9. filtrationThe solution was filtered
10. customthe solvent removed in vacuo

ORD record

ord-15ac8a85680d495e85f4e1fb1e0a4755

Source dataset

uspto-grants-1993_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05216020