1-(2,3-dihydro-1H-inden-2-yl)-2-methylpropan-2-amine

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of ethyl 3-{3,4-difluoro-5-[(1S)-1-hydroxy-2-iodoethyl]phenyl}propanoate (0.550 g, 1.43 mmol) in ethanol (2.8 mL) was added [2-(2,3-dihydro-1H-inden-2-yl)-1,1-dimethylethyl]amine (0.273 g, 1.44 mmol) and K2CO3 (0.218 g, 1.58 mmol). The reaction was heated at 90° C. for 17 h. Upon cooling, the reaction was filtered and concentrated. Column chromatography (0-12% CH3OH:CH2Cl2) provided 0.315 g (49%) of the title compound: MS (ESI) 446.0 (M+H). Upon cooling the reaction was filtered concentrated

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

Procedure: A mixture of methyl (2E)-3-(2-{(1R)-1-[(2R)-oxiran-2-yl methoxy]ethyl}phenyl)prop-2-enoate (342 mg, 1.30 mmol) described in WO 2004/106280, 1-(2,3-dihydro-1H-inden-2-yl)-2-methylpropan-2-amine (234 mg, 1.24 mmol) described in WO 01/53254, and lithium perchlorate (79 mg, 0.74 mmol) in toluene (12 mL) was stirred at room temperature for 16 hours. Water (10 mL) was added to the reaction solution, which was then extracted with ethyl acetate (10 mL×3). After that, the organic layers were combined, washed with saturated brine, and washed with anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate) to give the title compound as a colorless oily substance (206 mg, yield 37%). was then extracted with ethyl acetate (10 mL×3) washed with saturated brine washed with anhydrous magnesium sulfate The solvent was distilled off under reduced pressure The residue was purified by silica gel column chromatography (ethyl acetate)

Conditions: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of ethyl 3-{3,4-difluoro-5-[(1S)-1-hydroxy-2-iodoethyl]phenyl}propanoate (0.550 g, 1.43 mmol) in ethanol (2.8 mL) was added [2-(2,3-dihydro-1H-inden-2-yl)-1,1-dimethylethyl]amine (0.273 g, 1.44 mmol) and K2CO3 (0.218 g, 1.58 mmol). The reaction was heated at 90° C. for 17 h. Upon cooling, the reaction was filtered and concentrated. Column chromatography (0-12% CH3OH:CH2Cl2) provided 0.315 g (49%) of the title compound: MS (ESI) 446.0 (M+H). Upon cooling the reaction was filtered concentrated