tert-butyl N-(6-amino-2,3-dihydro-1H-inden-1-yl)carbamate

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Add MeI (0.623 g, 4.4 mmol) to a solution of N-4-fluorobenzyl-N-methylthioacetamide (0.662 g, 3.4 mmol) in 10 mL of ether at rt. Stir the mixture for 3 h and evaporate the ether under vacuum. Add (6-aminoindan-1-yl)carbamic acid tert-butyl ester (0.7 g, 2.28 mmol) followed by 5 mL of pyridine. Stir the resulting mixture for 12 h. Evaporate pyridine and purify the residue by column chromatography (silica gel, 3% MeOH in CH2Cl2) to give 1.26 g of (6-(1-((4-fluorobenzyl)methylamino)ethylideneamino)indan-1-yl)carbamic acid tert-butyl ester as a light yellow solid; MS 412 (MH+); 1H NMR (CD3OD) d 7.35-7.29 (2H, m), 7.18-7.10 (3H, m), 6.70 (1H, s), 6.65 (1H, d, J=7.6 Hz), 5.06 (1H, t, J=6.8 Hz), 4.69 (2H, s), 3.05 (3H, s), 2.97-2.91 (1H, m), 2.84-2.77 (1H, m), 2.55-2.48 (1H, m), 1.97 (3H, s), 1.52 (9H, s). evaporate the ether under vacuum Stir the resulting mixture for 12 h Evaporate pyridine and purify the residue by column chromatography (silica gel, 3% MeOH in CH2Cl2)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Add KBH4 (1.59 g, 29.4 mmol) slowly to a mixture of (6-nitro-indan-1-yl)carbamic acid tert-butyl ester (1.17 g, 4.2 mmol) and CuCl (1.25 g, 12.6 mmol) in 50 mL of methanol at 0° C. over 15 min. Stir the mixture for 1 h and then pass through a Florisil pad. Evaporate the THF and dissolve the solid in EtOAc. Wash the mixture with water, dry, and concentrate to afford 0.76 g (73%) of (6-aminoindan-1-yl)carbamic acid tert-butyl ester. 1H NMR (CDCl3) d 6.99 (1H, d, J=8.0 Hz), 6.65 (1H, s), 6.56 (1H, dd, J=8.0 and 2.0 Hz), 5.09 (1H, q, J=8.0 Hz), 4.70 (1H, br d, J=7.2 Hz), 3.60 (2H, s), 2.86-2.79 (1H, m), 2.75-2.67 (1H, m), 2.58-2.47 (1H, m), 1.78-1.69 (1H, m), 1.48 (3H, s). 2.86-2.79 (1H, m), 2.75-2.67 (1H, m), 2.58-2.47 (1H, m), 1.78-1.69 (1H, m), 1.48 (3H, s). Evaporate the THF dissolve the solid in EtOAc Wash the mixture with water dry concentrate