Aluminium lithium hydride → HCID 68616639, compound

Participants

Reaction Steps

To a ice-cooled solution of LiAlH4 (0.56 g, 14.76 mmol) in THF (25 mL), is added dropwise a solution of (3S*,4R*)-1-benzyl-4-hydroxymethyl-pyrrolidine-3-carboxylic acid isopropylamide (1.02 g, 3.69 mmol) in THF (5 mL). The reaction mixture is refluxed overnight and quenched with Na2SO4.10H2O (4 g) at 0° C. Ether is added, the mixture is stirred for 2 h at room temperature. The crude material is filtered over a pad of Celite and concentrated to give the title compound which is used without further purification in the next step. TLC, Rf (CH2Cl2/MeOH 95:5)=0.28. MS (LC-MS): 263.2 [M+H]+; ]+; tR (HPLC, C18 column, 10-100% CH3CN/H2O/5 min, 100% CH3CN/2.5 min, CH3CN and H2O containing 0.1% TFA, flow: 1.5 mL/min): 2.94 min.

Provenance & Evidence