methyl 4-amino-4-methylpentanoate

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

Procedure: 1-Cyano-4-hydroxy-7-phenoxyisoquinoline-3-carboxylic acid (47 mg, 0.15 mmol), N-ethylmorpholine (27 μL, 0.21 mmol), methyl 4-amino-4-methylpentanoate (crude as its acetic acid salt, 41 mg, 0.20 mmol), DCC (41 mg, 0.20 mmol) and HOBT (56 mg, 0.41 mmol) were suspended in CH2Cl2 (1 mL). The resulting mixture was stirred at room temperature for 20 hours. The reaction crude was filtered through a pad of celite and the filtrate was washed with sat'd NaHCO3 solution and H2O. The organic layer was dried over MgSO4, concentrated, and purified by flash chromatography (0-40% EtOAc/hexanes) to give the title compound in 12 mg. MS: (−) m/z 432.22 (M−1). The reaction crude was filtered through a pad of celite the filtrate was washed with sat'd NaHCO3 solution and H2O The organic layer was dried over MgSO4 concentrated purified by flash chromatography (0-40% EtOAc/hexanes)

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

Procedure: Methyl 4-methyl-4-nitropentanoate (0.8 g, 4.57 mmol) (Moffett (1963) Org. Syn. Coll. 4:652) and Pd/C (1 g, 10% by weight) were suspended in AcOH (15 mL). The resulting mixture was stirred under a hydrogen atmosphere at room temperature for 16 hours. The reaction mixture was then filtered through a pad of celite. The filtrate was concentrated and the crude was used in the subsequent step without further purification. MS: (+) m/z 146.12.91 (M+1). The reaction mixture was then filtered through a pad of celite The filtrate was concentrated the crude was used in the subsequent step without further purification