(R)-tert-butyl 3-(isopropylamino)pyrrolidine-1-carboxylate synthesis

Yield:820969-25-3 100%

Reaction Conditions:

with hydrogen;palladium 10% on activated carbon in ethanol at 20; under 3112.81 Torr; for 18 h;

Steps:

23

8.5g (45.6mmol, 1eq) of tert-butyl (3S)-3-aminopyrrolidine-1 -carboxylate, 30ml of acetone and 150ml of ethanol were mixed together. 2 g of 10% palladium on carbon were then added and the reaction mixture was hydrogenated under 415 kPa (about 60psi) of hydrogen, at room temperature, for 18 hours. The mixture was then filtered through CeI ite under a nitrogen atmosphere, and the solvent was removed under reduced pressure. 50 ml of toluene were added and the solvent was removed under reduced pressure, affording 10.4 g (100%) of the title product.¹HNMR(CDCI₃, 400MHz) δ: 1.05 (m, 6H), 1.42 (s, 9H), 1.65-1.90 (b, 2H), 2.10 (m, 1 H), 1.80-3.1 (m, 2H) 3.15-3.80 (m, 4H); LCMS ELSD-APCI⁺ m/z 229 [MH]⁺.

References:

WO2006/64336,2006,A2 Location in patent:Page/Page column 41