Compound A10

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InChIKey FYCBPDOYOODDOJ-DARIXABFSA-N

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

Lactam A6 (299 mg, 0.957 mmol) was dissolved in anhydrous methanol (6 mL) at room temperature. Then cerium(III) chloride (428 mg, 1.15 mmol) was added to the reaction vial and dissolved before the solution was cooled to 0 °C. After the reaction was cooled, sodium borohydride (354 mg, 9.57 mmol) was added in three portions at the start of the reaction. The reaction was allowed to stir at 0 °C for 2 hours before warming to room temperature on its own accord (ice bath was not removed) overnight. After 16 hours, a saturated solution of ammonium chloride was added slowly to the reaction vial to quench the reaction. The contents of the reaction mixture were transferred to a separatory funnel where dichloromethane was used to extract the product (3x). The organic layers were combined, dried with magnesium sulfate and concentrated to give a crude white foam. The crude diastereomers were purified via column chromatography using 100:0 to 95:5 dichloromethane/methanol to afford 144 mg (48% yield) of A10 as a white foam and 43 mg (14% yield) of A11 as a white foam. ¹H NMR (CDCl₃, 500 MHz): δ 7.30 (br m, 1H), 5.68 (s, 1H), 5.44 (m, 1H), 4.08 (d, J = 7.0 Hz, 1H), 3.20 (ddd, J = 13.6, 7.8, 4.8 Hz, 1H), 3.10 (ddd, J = 14.1, 8.9, 5.3 Hz, 1H), 2.76 (br s, 1H), 2.47 (td, J = 13.4, 4.3 Hz, 1H), 2.35 (dd, J = 15.0, 8.6 Hz, 1H), 2.22 - 2.05 (m, 5H), 2.04 - 1.93 (m, 3H), 1.63 (s, 3H), 1.58 (m, 1H), 1.40 (dd, J = 11.6, 8.5 Hz, 1H), 1.16 (s, 3H), 1.14 (m, 1H). ¹³C NMR (CDCl₃, 125 MHz): δ 170.4, 160.6, 134.0, 131.2, 120.1, 119.4, 67.5, 53.9, 45.1, 44.5, 43.3, 37.0, 35.8, 34.4, 33.2, 24.1, 22.4, 20.9, 12.1. HRMS(ESI): m/z calc. for C₁₉H₂₇N₂O₂ [M+H]⁺: 315.2073, found: 315.2072.