91 as a clear colorless liquid 13 c nmr cdcl 3 u03b4 132 6 132 5 69 0 62 7 56 6 40 2 31 8 22 1 anal calcd for c 8 h 18 no u00b7 0 175 h 8 no ammonium hydroxide c 64 21 h 10 88 n 11 34 found c 65 01 h 10 71 n 10 81 to a stirred solution of ethyl r 3 n benzyloxycarbonylpyrrolidin 2 yl 2 propenoate 3 03 g 10 00 mmol in anhydrous tetrahydrofuran 75 ml at u2212 78 u00b0 c under nitrogen was added dropwise a solution of diisobutylaluminum hydride 1 0 m in hexanes 22 0 ml 22 0 mmol 2 2 eq the resulting solution was stirred at u2212 78 u00b0 c under nitrogen for 30 minutes the reaction solution was then allowed to warm to room temperature over the course of 2 hours a saturated solution of sodium hydrogen carbonate 50 ml was added and the aqueous mixture was extracted with ethyl acetate 3 u00d7 50 ml the extracts were combined dried mgso 4 and evaporated under reduced pressure column chromatography of the residue with diethyl ether hexanes 1 1 afforded the title compound as a clear colorless oil 1 41 g 5 40 mmol 54 1 h nmr cdcl 3 u03b4 7 40 7 25 m 5h 5 75 5 53 m.