Sodium Bicarbonate → (R)-1-(N-Benzyloxycarbonylpyrrolidin-2-yl)-3-hydroxypropene

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of (R)-ethyl 3-(N-benzyloxycarbonylpyrrolidin-2-yl)-2-propenoate (see WO-A-92/06973, Example 13A) (10.00 mmol) in anhydrous tetrahydrofuran (75 mL) at -78° C. under nitrogen was added dropwise a solution of diisobutylaluminium hydride (1.0 M in hexanes, 12.0 mL, 22.0 mmol, 2.2 eq). The resulting solution was stirred at -78° 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 (3×50 mL). The extracts were combined, dried (MgSO4), 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: 1H NMR (CDCl3) δ 7.40-7.25 (m, 5H), 5.75-5.53 (m, 2H), 5.20-5.00 (m, 2H), 4.38 (br m, 1H), 4.06 (br d, J=13.7 Hz, 2H), 3.45 (br t, J=7.0 Hz, 1H), 2.03-1.68 (m, 4H); [α]25 =+34° (MeOH, c=1.0); HRMS: calculated for C15H19NO3 261.1365, found 261.1356.

Provenance & Evidence