Sodium Carbonate → 2-Aminoindane

A mixture of 2-amino-indane hydrochloride (10 g, 58.9 mmol) and EtOAc was treated with 2 M aqueous Na2CO3 solution. The organic layer was separated and washed (2 M aqueous Na2CO3 solution); the aqueous layers were extracted with EtOAc. The combined organic phases were washed (saturated aqueous NaCl solution), dried (MgSO4), filtered, and concentrated to give 2-amino-indane (7.8 g), which was dissolved in dry THF (80 ml). 4-Nitrobenzaldehyde (9.74 g, 64.4 mmol) and acetic acid (3.35 ml, 58.6 mmol) were added. The mixture was stirred at room temperature for 1 hour. NaBH(OAc)3 (37.2 g, 176 mmol) was added. The resulting yellow suspension was stirred for 15 hours (over night). The mixture was poured onto EtOAc and 2M aqueous Na2CO3 solution (gas evolution). The organic phase was separated, washed (2M aqueous Na2CO3 solution, saturated. aqueous NaCl solution), dried (Na2SO4), filtered and concentrated. Flash chromatography (hexane/EtOAc 7:3) afforded 14.76 g (94%) of intermediate 15.

1. customThe organic layer was separated
2. washwashed (2 M aqueous Na2CO3 solution)
3. extractionthe aqueous layers were extracted with EtOAc
4. washThe combined organic phases were washed (saturated aqueous NaCl solution)
5. dry with materialdried (MgSO4)
6. filtrationfiltered
7. concentrationconcentrated

ORD record

ord-090a330cfbae4cb395837cb854e6e37c

Source dataset

uspto-grants-2011_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07947694B2