Tetrahydrofuran → {(S)-4-[4-(6-Amino-5-benzothiazol-2-ylpyridin-3-yl)-pyrazol-1-yl]-pyrrolidin-2-yl}-methanol

Participants

Reaction Steps

A solution of (2S,4S)-4-[4-(6-amino-5-benzothiazol-2-ylpyridin-3-yl)-pyrazol-1-yl]-pyrrolidine-2-carboxylic acid (10.0 mg, 0.0155 mmol) in THF (4 mL, 0.05 mol) was cooled to −78° C. LiAlH4 (1.0 M in THF; 0.2 mL, 0.2 mmol) was added slowly, and the mixture was allowed to warm to rt overnight. The material was concentrated in vacuo, then dissolved in DCM, transferred to a separatory funnel, and washed with sat. NaHCO3. The organic layer was loaded onto a prep TLC plate, eluting with 8% (7N NH3 in MeOH)/DCM. The band containing the product was filtered off using 1:1 MeOH/DCM. The filtrate was concentrated in vacuo to afford the title compound (mixture of diastereomers) as a yellow solid. MS (ES+): m/z=393.14 [MH+].

Provenance & Evidence