tert-butyl 4-oxohexahydrocyclopenta[c]pyrrole-2(1H)-carboxylate synthesis

Yield: 98%

Reaction Conditions:

with hydrogen;Pearlman's catalist in ethanol under 2585.81 Torr; for 20 h;

Steps:

1
To a solution of 1 (2.00 g, 9.3 mmol) in EtOH (100 mL) was added di- tert-butyl dicarbonate (2.29 g, 10.5 mmol) and Pd(OH)₂ZC (250 mg). An atmosphere of H₂ (50 psi) was secured using a Parr-shaker and reacted for 20 h. The reaction mixture was filtered through celite and concentrated under vacuum to afford 2 as a pale yellow oil (2.05 g, 98%); ¹H-NMR (400 MHz, CDCl₃) δ 3.81-3.42 (m, 3H), 3.20-3.11 (m, IH), 3.09-3.01 (m, IH), 2.79-2.68 (m, IH), 2.37 (t, J = 8.0 Hz, 2H), 2.25-2.16 (m, IH), 1.93-1.79 (m, IH), 1.46 (s, 9H); m/z 170.1 [M-¹Bu].

References:

VANDERBILT UNIVERSTIY;LINDSLEY, Craig, W.;CONN, P., Jeffrey;WEAVER, Charles, David;NISWENDER, Colleen, M.;WILLIAMS, Richard;JONES, Carrie, K.;SHEFFLER, Douglas, J. WO2010/68851, 2010, A1 Location in patent:Page/Page column 62