Cyclohexane → HCID 68857440, compound

Temperature

0 °C

K3[Fe(CN)6] (0.98 g, 3 mmol, 3 eq), K2CO3 (0.412 g, 3 mmol, 3 eq), quinuclidine (0.004 g, 0.01 mmol, 0.01 eq), OSO4 (0.003 mL, 0.01 mmol, 0.01 eq), H2O, (5 mL) and tBuOH, (5 mL) were added to a round bottomed flask and stirred until the solution went clear. Methansulfonamide (0.095 g, 1 mmol, 1 eq) was added, the mixture cooled to 0° C. and the diene of Example 25 (0.152 g, 1 mmol, 1 eq) was introduced with vigorous stirring. The mixture was then stirred at room temperature for 48 hours, before sodium sulfite (1 g) was added and stirred for 45 minutes. The reaction mixture was extracted with EtOAc (3×20 mL) and the combined extracts washed with 10% NaOH (20 mL) and brine (20 mL), then dried over MgSO4 and the solvent removed in vacuo. Column chromatography (cyclohexane:EtOAc, 60:40, Rf=0.25) furnished the product as a colourless oil (0.118 g, 0.63 mmol, 63% yield); 1H NMR (400 MHz, CDCl3) 5.56 (1H, m, H-3), 5.50 (1H, m, H-4), 3.94 (1H, m, H-7), 3.81 (1H, m, H-6), 2.35 (1H, m, H-5), 1.86 (1H, m, H-5′), 1.86 (1H, m, H-2), 0.07 (9H, s, H-1); 13C NMR (100 MHz, CDCl3) δ 125.19 (C-4), 120.82 (C-3), 70.39 (C-6), 68.30 (C-7), 35.73 (C-2), 30.16 (C-5), −2.42 (C-1); IR (neat, cm−1) 3423 (b, OH) 1640 (b, C═C) MS (ESI-, m/z) 185.25 [M−H+].

1. additionwas added
2. stirringstirred for 45 minutes
3. extractionThe reaction mixture was extracted with EtOAc (3×20 mL)
4. washthe combined extracts washed with 10% NaOH (20 mL) and brine (20 mL)
5. dry with materialdried over MgSO4
6. customthe solvent removed in vacuo

ORD record

ord-afd94cfba4a248448f9c65b4232e41d7

Source dataset

uspto-grants-2009_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07572928B2