Triethylamine → (2S,4R)-tert-butyl 4-(5-cyclopropylpyrazin-2-yloxy)-2-((2-methoxy-2-oxoethylamino)methyl)pyrrolidine-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

A solution of the product from Example 174D (2 g, 5.98 mmol) in methanol (3 mL) was treated with triethylamine (1.834 mL, 13.16 mmol) and methyl 2-bromoacetate (0.608 mL, 6.58 mmol), and the mixture was stirred at 65° C. for 3 hours. The resulting material was partitioned between water and ethyl acetate. The organic extract was dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by flash chromatography on a 24 g silica gel column eluting with 5% ethyl acetate/hexanes for 3 minutes then a gradient to 100% ethyl acetate over 20 minutes to afford the title compound as a colorless oil (1.10 g, 45.2%).

Provenance & Evidence