HCID 14804750, compound → (3R,4R)-3-amino-1-hydroxy-4-methylpyrrolidin-2-one

Participants

Reaction Steps

(3R,4R)-1-Benzyloxy-4-methyl-3-[(R)-1-phenylethylamino]pyrrolidin-2-one (6.4 g. 19.7 mmol) was hydrogenolysed on Pearlman's catalyst (1.6 g) in methanol (100 ml) and acetic acid (2 ml) for 2 h at 50 psi. After filtration and evaporation, the residue was dissolved in water and applied to a column containing DOWEX 50W-X8 (100-200 mesh, 4×4 cm, H+ form). After washing the resin with water (150 ml) the product was eluted with dilute aqueous ammonia. The fractions containing the product were freeze dried to give (3R,4R)-3-amino-1-hydroxy-4-methylpyrrolidin-2-one (2.3 g, 90%) as a white foam. [α]D =+16.3° (c=0.48, MeOH). The 1H NMR of this product was identical to that of the racemate. To the foam was added D-(-)-tartaric acid (1.33 g), the solids dissolved in water, and freeze dried to give (3R,4R)-3-amino-1-hydroxy-4-methylpyrrolidin-2-one, (-)tartrate salt (3.91 g). 1H NMR (360 MHz, D2O) 4.36 (1 H, s, CHOH), 4.24 (1 H, d, J=8.4 Hz, CHN), 3.90 H(1H, dd, J=6.6 and 9.5 Hz, NCHAHB), 3.34 (1 H, dd, J=2.2 and 9.5 Hz, NCHAHB), 2.8-3.0 (1 H, m, CHCH3), 1.74 (3 H, d, J=7.1 Hz, CH3), m/z (CI, NH3) 131 (M+ +H) (Found: C, 38.09; H, 6.65; N, 12.65. C7H13N2O5 +0.9 H2O requires C, 37.97; H, 6.73, N, 12.65). Analysis by HPLC on a chiral stationary phase found enantiomeric purity of 99.66%.

Provenance & Evidence