Potassium Sodium Tartrate → HCID 86758478, compound

Participants

Reaction Conditions

Reaction Steps

Diisopropyl azodicarboxylate (80 mL, 0.40 mmol) was added to an efficiently stirred solution of triphenylphosphine (105 mg, 0.40 mmol) in 1 mL of THF at 0° C. The mixture was stirred at 0° C. for 30 min during which time a white precipitate formed. A mixture of compound 54 (0.20 mmol, 59 mg) and 28.2 μL(0.4 mmol) of thiolacetic acid in 0.5 mL of THF was added dropwise, and the mixture was stirred at 0° C. for 1 h and then at 25° C. for 2 h. The solution was concentrated. Ether (5 mL) was added, and the ether solution was acidified with 10% HCl. The water layer was extracted with ether and neutralized with saturated NaHCO3. The resulting solution was extracted with CH2Cl2, and the organic layer was washed with brine, dried, and concentrated to give 50 mg of the crude product. To the solution of the crude thioester (crude, 50 mg, 0.15 mmol) in 5 mL of THF was added portionwise LiAlH4(18 mg, 0.45 mmol). The mixture was stirred at room temperature for 2 h then a saturated solution of Rochelle salt (1.8 mL) was added followed by extraction with EtOAc. The organic phase was washed with brine, dried, and concentrated. Flash chromatography of the residue afforded the title compound (17 mg, 26% overall for the two steps): [α]D +40.0((c 1.40, CHCl3);1H NMR (CDCl3) d 0.92-1.08 (m, 1H), 1.10-1.30 (m, 2H), 1.32-1.64 (m, 2H), 1.64-1.90 (m, 4H), 1.93-2.18 (m, 2H), 2.22-2.50 (m, 5H), 2.95 (d, 1H, J=10.8 Hz), 3.06 (d, 1H, J=10.5 Hz), 7.05-7.15 (m, 2H), 7.20-7.32 (m, 2H); 13C NMR (CDCl3) 24.8, 30.7, 31.4, 35.1, 41.0, 46.7, 48.3, 56.4, 61.7, 128.9, 129.2, 132.1, 143.6; MS m/z 44 (26), 250 (100), 282 (M+, 2); Anal. (C15H22ClNS) Calcd: C 63.47, H 7.81, N 4.93; Found: C 63.85, H 7.89, N 4.76.

Provenance & Evidence