Pivaloyl chloride → (8aS)-7-(2,2-Dimethylpropyl)-2-[(1S,2R)-2-phenylcyclopropyl]tetrahydro imidazo[1,5-a]pyrazine-1,3(2H,5H)-dione

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Reaction Conditions

Reaction Steps

To a stirred solution of Example 4, D2 (1 eq) and TEA (1.1 eq) in DCM (0.08M) was added pivaloyl chloride (2.1 eq) and the reaction mixture was stirred at 25° C. for 2 h. The crude product was purified by preparative RP-HPLC using H2O (0.1% TFA) and MeCN (0.1% TFA) as eluents, affording the title compound. 1H NMR (400 MHz, DMSO-d6, 300K) 7.48-7.18 (5H, m), 4.75-4.63 (1H, m), 4.42-4.33 (1H, m), 4.05-3.93 (2H, m), 3.15-2.80 (3H, m), 2.72-2.63 (1H, m), 2.50-2.38 (1H, m), 1.58-1.51 (1H, m), 1.48-1.38 (1H, m), 1.35 (9H, s). MS (ES) C20H25N3O3 requires: 354 found: 355 (M+H)+.

Provenance & Evidence