Stannous chloride dihydrate → (1R)-5-Bromo-2,3-dihydro-1H-inden-1-amine

A solution of (R)-1-azido-5-bromo-indane (14.0 g, 58.8 mmol) was dissolved in methanol (150 mL) and was treated with SnCl2.2H2O (23.0 g, 106 mmol). The mixture was stirred at room temperature overnight (TLC indicated no starting material) and was concentrated to dryness. The resulting residue was treated with 2N aqueous NaOH (300 mL) and was extracted with EtOAc (2×300 mL). The combined organic extracts were washed with 1N HCl followed by water (2 L). The pH of the combined aqueous layers was adjusted to 11 with cold saturated NaOH solution and the mixture was extracted with EtOAc (2×300 mL). The combined organic extracts were dried over Na2SO4, filtered and concentrated to give 10.0 g (80%) of (1R)-5-bromoindan-1-amine as a dark yellow oil which solidified upon refrigeration. MS (ES+) 213.9 (M+H)+. 1H NMR (CDCl3) δ 1.70-1.75 (m, 1H), 2.40-2.45 (m, 1H), 2.77-2.82 (m, 1H), 2.93-2.97 (m, 1H), 4.28-4.33 (m, 1H), 7.18-7.23 (m, 1H), 7.36-7.41 (m, 2H).

1. concentrationwas concentrated to dryness
2. additionThe resulting residue was treated with 2N aqueous NaOH (300 mL)
3. extractionwas extracted with EtOAc (2×300 mL)
4. washThe combined organic extracts were washed with 1N HCl
5. extractionthe mixture was extracted with EtOAc (2×300 mL)
6. dry with materialThe combined organic extracts were dried over Na2SO4
7. filtrationfiltered
8. concentrationconcentrated

ORD record

ord-6f3294ae9fdd4aff8e0c7b81140f9486

Source dataset

uspto-grants-2013_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08609680B2