Isopropanol → (3R,4S)-3-amino-4-(3-boronopropyl)-1-(7H-purin-6-yl)pyrrolidine-3-carboxylic acid

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Reaction Conditions

Reaction Steps

A stirred solution of (3R,4S)-3-acetamido-N-tert-butyl-4-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propyl)pyrrolidine-3-carboxamide (Example 8, step 4) (198 mg, 0.5 mmol) in anhydrous 2-propanol (5 mL) was treated with 6-chloropurine (92 mg, 0.6 mmol) and diisopropylethylamine (0.174 mL, 1.0 mmol), heated to 80° C. for 18 h, then diluted with methylene chloride (20 mL). The mixture was filtered through Celite® and the filtrate concentrated. The crude material was deprotected and isolated using the method described for example 8, step 5 to afford (3R,4S)-3-amino-4-(3-boronopropyl)-1-(7H-purin-6-yl)pyrrolidine-3-carboxylic acid (41 mg, 20%) as a pale amber solid. NMR (D2O) δ 8.20-8.45 (m, 2 H), 4.20-4.60 (m, 2 H), 3.50-4.00 (m, 2 H), 2.60-2.80 (m, 2 H), 1.65 (m, 1 H), 1.20-1.55 (m, 3 H), 0.65-0.75 (m, 2 H). MS (m+1): 335.2; MS (m−H2O+1): 317.1.

Provenance & Evidence