Triethylamine → (S)-N-Methyl-2,3-dihydro-1H-inden-1-amine

To a solution of (S)-(+)-1-aminoindan (176 mg, 1.29 mmol) in THF (10.0 mL) was added Et3N (0.200 mL, 1.43 mmol) followed by di-tert-butyldicarbonate (286 mg, 1.31 mmol). The mixture was stirred under an atmosphere of nitrogen for 3 days, concentrated, diluted with DCM (100 mL), and washed with 0.1 N aq hydrochloric acid (50.0 mL) and aq NaCl. The organic layer was dried (MgSO4), filtered and concentrated. The tan solid was taken up in tetrahydrofuran (10.0 mL) and to this was added with a 1.00 M solution of lithium aluminum hydride (1.0 M in THF, 5.80 mL). The mixture was heated at reflux for 6 hours, quenched with water (0.300 mL), 15% aq NaOH solution (0.300 mL) and water (0.900 mL). This was stirred for 10 minutes, filtered through celite, diluted with EtOAc (100 mL), dried (MgSO4), filtered and concentrated. The residue was purified via flash chromatography (0 to 100% EtOAc/hexanes to 10% MeOH/DCM) to afford the title compound as a black solid (146 mg, 77%).

1. concentrationconcentrated
2. additiondiluted with DCM (100 mL)
3. washwashed with 0.1 N aq hydrochloric acid (50.0 mL) and aq NaCl
4. dry with materialThe organic layer was dried (MgSO4)
5. filtrationfiltered
6. concentrationconcentrated
7. additionto this was added with a 1.00 M solution of lithium aluminum hydride (1.0 M in THF, 5.80 mL)
8. temperatureThe mixture was heated
9. temperatureat reflux for 6 hours
10. customquenched with water (0.300 mL), 15% aq NaOH solution (0.300 mL) and water (0.900 mL)
11. stirringThis was stirred for 10 minutes
12. filtrationfiltered through celite
13. additiondiluted with EtOAc (100 mL)
14. dry with materialdried (MgSO4)
15. filtrationfiltered
16. concentrationconcentrated
17. customThe residue was purified via flash chromatography (0 to 100% EtOAc/hexanes to 10% MeOH/DCM)

ORD record

ord-8ea25896b2a744c4af4acf12a6d65beb

Source dataset

uspto-grants-2011_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07951810B2