(3R,5S)-5-(methoxymethyl)pyrrolidin-3-ol

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To (2S,4R)-2-Methoxymethyl-4-trimethylsilanyloxy-pyrrolidine-1-carboxylic acid benzyl ester 1.00 g (3.98 mmol) in 3 mL of methanol was added 10% Pd(C) 0.10 g and the mixture was stirred under 1 atmosphere of hydrogen for 24 h. The mixture was filtered through a 0.22 μM Teflon filter, concentrated and subsequently put on a high vacuum for 2 h to afford 0.43 g (86%) of (3R,5S)-5-Methoxymethyl-pyrrolidin-3-ol as clear oil. 1H NMR (CDCl3, 400 MHz) δ: 5.30 (1H, s), 4.67 (1H, t, J=5.6 Hz), 4.56 (1H, t, J=7.6 Hz), 4.26-4.21 (1H, m), 4.19 (1H, dd, J=8.1, 3.3 Hz), 3.14 (1H, d, J=12.3 Hz), 2.08 (1H, dd, J=8.2, 3.2 Hz), 1.66-1.59 (3H, m). LCMS (ACPI) (M+H+) m/z: 132.2. The mixture was filtered through a 0.22 μM Teflon filter concentrated