Carbamic acid, N-(3-azabicyclo[3.1.0]hex-6-ylmethyl)-, 1,1-dimethylethyl ester synthesis

Yield:871727-12-7 73%

Reaction Conditions:

with ammonium formate;palladium 10% on activated carbon in ethanol at 20; for 2 h;

Steps:

3.4

10% Pd/C (2.35g) and ammonium formate (2.35g) were added to a stirred solution of tert-butyl (S-benzyl-S-azabicyclop.i .Ojhex-δ-yOmethylcarbamate (2.35g, 7.78mmol) and EtOH (90ml) at r.t. and the reaction stirred for 2 h. The suspension was then filtered through celite and the filtrate concentrated in vacuo. DCM (100ml) was added to the resultant gummy white solid and the mixture filtered. The filtrate was concentrated in vacuo to give the title compound as a yellow oil (1.2g, 73%). LCMS purity 95%, m/z 213 [M+H]⁺, ¹H NMR (300 MHz, CDCI₃) δ: 0.89 (1H, m), 1.26 (2H, m), 1.47 (9H, s), 2.96 (2H, d, J = 11.4 Hz), 3.07 (4H, m), 4.62 (2H, br s).

References:

WO2006/123121,2006,A1 Location in patent:Page/Page column 18; 33