Lithium borohydride → HCID 86679640, compound

Participants

Reaction Conditions

Reaction Steps

Lithium borohydride (12.7 g, 4 eq) was added portionwise to a solution of (3S,4R)-4-methoxy-pyrrolidine-1,3-dicarboxylic acid 1-tert-butyl ester 3-methyl ester (35.81 g, 138.1 mmol) in THF (600 mL), then the reaction was heated to 60° C. for 4 hrs. The reaction was quenched with water at 0° C. and extracted with EtOAc. The organic layer was washed with sat. NaCl and dried over Na2SO4. The solvent was removed and the residue was purified through a plug of SiO2 (3:1 EtOAc/heptane) to yield the title compound as a clear oil (29.35 g, 92% yield). 1H NMR (400 MHz, chloroform-d) δ ppm 1.46 (s, 9H) 2.37-2.47 (m, 1H) 3.19 (dd, J=11.08, 5.29 Hz, 1H) 3.33 (d, J=4.03 Hz, 4H) 3.50-3.66 (m, 4H) 3.77-3.83 (m, 1H). m/z (APCI+) for product minus Boc (C6H13NO2) 132.2 (M+H)+. Specific Rotation: [a]D=+9.3 degrees (C=0.86, MeOH).

Provenance & Evidence