6-Benzenesulfonyl-1,2,3,4-tetrahydro-naphthalene-1-carbonitrile → C-(6-benzenesulfonyl-1,2,3,4-tetrahydro-naphthalen-1-yl)-methylamine

6-Benzenesulfonyl-1,2,3,4-tetrahydro-naphthalene-1-carbonitrile was dissolved in 100 mL of dry tetrahydrofuran (THF), and the mixture was stirred while cooling in an ice bath. Borane-THF complex (40 mL) was added to the cold, stirring solution, and the reaction mixture was stirred under nitrogen for 15 hours at room temperature. The reaction mixture was carefully quenched by addition of 20 mL of 20% HCl and 60 mL of methanol. The solvents were removed under reduced pressure, and the aqueous residue was treated dropwise with 1M NaOH until basic. The residue was extracted twice with 100 mL of EtOAc and the organic layers were dried (MgSO4) and evaporated. The crude product was acidified with dilute HCl in EtOH and recrystallized from EtOAc to yield 3.1 g of C-(6-benzenesulfonyl-1,2,3,4-tetrahydro-naphthalen-1-yl)-methylamine as a hydrochloride salt. MS: 302 (M+H)+.

1. temperaturewhile cooling in an ice bath
2. additionBorane-THF complex (40 mL) was added to the cold
3. stirringstirring solution
4. stirringthe reaction mixture was stirred under nitrogen for 15 hours at room temperature
5. customThe reaction mixture was carefully quenched by addition of 20 mL of 20% HCl and 60 mL of methanol
6. customThe solvents were removed under reduced pressure
7. additionthe aqueous residue was treated dropwise with 1M NaOH until basic
8. extractionThe residue was extracted twice with 100 mL of EtOAc
9. dry with materialthe organic layers were dried (MgSO4)
10. customevaporated
11. customrecrystallized from EtOAc

ORD record

ord-171ebfb9c9064fbea30a1ee511c18e93

Source dataset

uspto-grants-2007_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07312359B2