Compound 2

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InChIKey MZKFVSWBNGFPPC-UHFFFAOYSA-N

Synthetic procedure: See article for the definitive version of this procedure and for full experimental details.

Sodium hydride (160 mg of a 60% suspension in mineral oil, 4.00 mmol, 1.10 equiv) was washed with pentane (3 x 2 mL) and suspended in DMF (20 mL). The suspension was cooled to 0 °C and commercially available alcohol 25 (550 mg, 3.64 mmol, 1.00 equiv) in DMF (8 mL) was added dropwise over 5 min. The resulting suspension was allowed to warm to rt. After 1 h, the reaction mixture was cooled to 0 °C and tributyl(iodomethyl)stannane (20; 1.57 g, 3.64 mmol, 1.00 equiv) in DMF (8 mL) was added dropwise over 10 min. The suspension was allowed to warm to rt over 1 h, and then stirred at rt for 2 h. The reaction mixture was cooled to 0 °C and slowly quenched with sat aq NH₄Cl (10 mL). The layers were separated and the aqueous layer was extracted with EtOAc (3 x 20 mL). The combined organic layers were washed with H₂O (2 x 10 mL), brine (10 mL), dried over Na₂SO₄, filtered, and concentrated under reduced pressure. Purification by flash column chromatography (cyclohexane/EtOAc 4:1 + 0.1% Et₃N v/v) afforded the pure SnAP-PhOA 2 (1.26 g, 76% yield) as clear, pale yellow liquid. IR (thin film): ν 3384, 2955, 2925, 2870, 1455, 1376, 1087 cm^-1; ¹H NMR (400 MHz, CDCl₃): δ 7.36-7.28 (m, 4H), 7.26-7.20 (m, 1H), 4.07 (dd, J = 7.3, 6.3 Hz, 1H), 3.68 (s, J(^117/119Sn-¹H) = 14.2 Hz, 2H), 3.41-3.34 (m, 1H), 3.32-3.24 (m, 1H), 1.95-1.82 (m, 2H), 1.76 (br s, NH₂), 1.60-1.42 (m, 6H), 1.35-1.26 (m, 6H), 0.96-0.81 (m, 15H); ¹³C NMR (100 MHz, CDCl₃): δ 146.6, 128.6, 127.0, 126.5, 73.3, 62.2, 53.9, 39.5, 29.3, 27.5, 13.9, 9.1; ESI-HRMS calcd for C₂₂H₄₂N₁O₁Sn₁ [M + H] 456.2287, found 456.2300.