4-amino-4-methylpentan-1-ol

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

Procedure: 5-Cyclopropyl-6-cyclopropylmethoxy-pyrazine-2-carboxylic acid (Example 10 g, 100 mg, 0.43 mmol) was suspended in DMF (3 mL). Mukaiyama Reagent (CAN 878-23-9, 233.8 mg, 0.85 mmol), DIEA (0.31 mL, 2.24 mmol) and 4-amino-4-methyl-pentan-1-ol (CAN 85054-53-1, 101.33 mg, 0.64 mmol) were added and the reaction mixture was stirred at room temperature for 12 hours. The mixture was extracted with ethyl acetate and water; the organic phase was dried over Na2SO4, filtered and concentrated in vacuo. The crude material was purified by reverse phase preparative HPLC (Xterra-RP18, 10 μ, 19×250 mm/acetonitrile/10 mM ammonium acetate in water) to give the desired product (100 mg, 70.26%) as colorless sticky liquid; LC-MS (UV peak area, ESI) 96.12%, 334.0 (M+H). The mixture was extracted with ethyl acetate and water the organic phase was dried over Na2SO4 filtered concentrated in vacuo The crude material was purified by reverse phase preparative HPLC (Xterra-RP18, 10 μ, 19×250 mm/acetonitrile/10 mM ammonium acetate in water)