Compound 1

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InChIKey MFLUZZMSFDSMIZ-UHFFFAOYSA-N

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

To a solution of 22 (1.27 g, 2.50 mmol, 1.00 equiv) in EtOH (10 mL) was added hydrazine monohydrate (1.21 mL, 25.0 mmol, 10.0 equiv). The reaction mixture was refluxed for 20 min while colorless solid crashed out. The solvent was removed under reduced pressure. The resulting residue was suspended in CH₂Cl₂ and filtered over Celite. The organic filtrate was concentrated under reduced pressure to afford pure SnAP-OA 1 in quantitative yield (860 mg) as clear, colorless liquid. IR (thin film): ν 2955, 2924, 2870, 2853, 1576, 1463, 1375, 1338, 1089 cm^-1; ¹H NMR (400 MHz, CDCl₃): δ 3.70 (s, J(^117/119Sn-¹H) = 7.2 Hz, 2H), 3.39 (t, J = 6.0 Hz, 2H), 2.76 (t, J = 6.8 Hz, 2H), 1.69 (quint, J = 6.4 Hz 2H), 1.63-1.40 (m, 6H), 1.39-1.15 (m, 8H), 1.02-0.77 (m, 15H); ¹³C NMR (100 MHz, CDCl₃): δ 73.9, 62.2, 40.1, 33.8, 29.3, 27.4, 13.9, 9.2; ESI-HRMS calcd for C₁₆H₃₈N₁O₁Sn₁ [M + H] 380.1972, found 380.1975.