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With carbon tetrabromide; triphenylphosphine; In acetonitrile; at 0 - 20℃; for 24h;
Example 8Example 8, Step aTo a suspension of (R)-5-(hydroxymethyl)pyrrolidin-2-one (5 g, 43.4 mmol) and triphenylphosphine (17.09 g, 65.1 mmol) in acetonitrile (300 mL) at 0 C in an ice-water bath was added dropwise a solution of carbontetrabromide (21.60 g, 65.1 mmol) in acetonitrile (80 mL). The suspension gradually changed to clear solution in 1 hour and the bath was removed and stirred at room temperature for 23 hrs. The solvent was removed in vacuo and the resultant crude material was submitted to flash chromatography (30- 100% EtOAc/Hexane, 10-20% MeOH/EtOAc) to affordExample 8, Step a as brown oil (6.3 g). LC (Cond. II): RT = 1.29 min; LC/MS: Anal. Calcd. for [M+H]+ C5H9BrNO: 179.99; found: 178.1 1. 1H NMR (CDCI3, delta = 7.26 ppm, 400 MHz) delta 6.09 (br. s., 1H), 4.07 - 3.92 (m, 1H), 3.46 (dd, J=10.3, 4.8 Hz, 1H), 3.36 (dd, J=10.3, 7.5 Hz, 1H), 2.55 - 2.30 (m, 3H), 1.99 - 1.81 (m, 1H).
With tetrakis(triphenylphosphine) palladium(0); carbon tetrabromide; In acetonitrile; at 0 - 20℃; for 24h;
To a suspension of (R)-5-(hydroxymethyl)pyrrolidin-2-one (5 g, 43.4 mmol) and triphenylphosphine (17.09 g, 65.1 mmol) in acetonitrile (300 mL) at 0 C in an ice-water bath was added dropwise a solution of carbontetrabromide (21.60 g, 65.1 mmol) in acetonitrile (80 mL). The suspension gradually changed to clear solution in 1 h and the bath was removed and stirred at room temperature for 23 h. The solvent was removed in vacuo and the resultant crude material was submitted to flash chromatography (30- 100% EtOAc/Hexane, 10-20% MeOH/EtOAc) to afford Example 8, Step a as brown oil (6.3 g). LC (Cond. II): Rt = 1.29 min; LC/MS: Anal. Calcd. for [M+H]+ C5H9BrNO: 179.99; found: 178.11. 1H NMR (CDCl3, delta = 7.26 ppm, 400 MHz) delta 6.09 (br. s., 1H), 4.07 - 3.92 (m, 1H), 3.46 (dd, J=10.3, 4.8 Hz, 1H), 3.36 (dd, J=10.3, 7.5 Hz, 1H), 2.55 - 2.30 (m, 3H), 1.99 - 1.81 (m, 1H).
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