4-Amino-2,2,6,6-tetramethylpiperidine → HCID 86761155, compound

Participants

Reaction Steps

(S)-2-{[(S)-1-(3-Fluoro-benzenesulfonyl)-piperidine-2-carbonyl]-amino}-3-[4-(3-fluoro-propoxy)-phenyl]-propionic acid (80 mg, 0.16 mmol), 4-amino-2,2,6,6-tetramethylpiperidine (25 mg, 0.16 mmol), 1-hydroxybenzotriazole (30 mg, 0.22 mmol) and 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (39 mg, 0.20 mmol) were mixed in dichloromethane (2 mL). The mixture was stirred overnight at room temperature. The reaction mixture was diluted with dichloromethane and washed twice with a saturated aqueous sodium bicarbonate solution, and the organic fraction dried over magnesium sulfate. After filtration and subsequent concentration, the resulting oil was chromatographed (dichloromethane/methanol, 9/1) on silica gel to produce 27 mg (27%) of the title compound. MS: m/e 649.33 (M+H). 1H NMR (300 MHz, d6-DMSO): δ0.70-2.20 (m, 27H), 2.80 (m, 2H), 3.20 (m, 1H), 3.65 (d, 1H, J=12 Hz), 4.00 (m, 3H), 4.30 (q, 1H, J=6 Hz), 4.50 (m, 2H), 4.65 (t, 1H, J=6 Hz), 6.90 (d, 2H, J=9 Hz), 7.15 (d, 2H, J=9 Hz), 7.50 (m, 4H), 8.00 (m, 2H).

Provenance & Evidence