Aluminium lithium hydride → 2,6-Di-tert-butyl-4-[4-(2-hydroxy-ethyl)-1-(5-hydroxymethyl-1-methyl-1H-pyrrole-2-sulfonyl)-piperidin-4-ylsulfanyl]-phenol

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Reaction Steps

To 5-[4-(2-acetoxy-ethyl)-4-(3,5-di-tert-butyl-4-hydroxy-phenylsulfanyl)-piperidine-1-sulfonyl]-1-methyl-1H-pyrrole-2-carboxylic acid methyl ester (Ex. 1d, 460 mg, 0.75 mmol) in 4 mL of THF was added dropwise 3 mL of a 1 M LiAlH4 in THF. The mixture was stirred for 2 h and then quenched with saturated aqueous NaH2PO4 (20 mL). It was diluted with Ethyl acetate (30 mL), stirred for 10 min, and then let sit for 1 h. The layers were separated and the aqueous layer was extracted with Ethyl acetate (20 mL). The combined organic layers were washed with water (50 mL), dried over Na2SO4, and concentrated under reduced pressure. The crude product was chromatographed with 10-85% Ethyl acetate/hexanes to afford the title compound as a white solid (305 mg, 75%), mp 126-127° C. 1H NMR (400 MHz, CD3OD): δ 7.26 (d, J=2.0 Hz, 1H), 7.15 (s, 2H), 6.34 (d, J=2.0 Hz, 1H), 4.57 (s, 2H), 3.88 (t, J=7.2 Hz, 2H), 3.76 (s, 3H), 3.26 (1H), 3.02 (td, J=7.2, 2.4 Hz, 2H), 1.75-1.68 (m, 2H), 1.64-1.58 (m, 4H), 1.39 (s, 3H); ESI/CI-MS m/z 539 ([M+H]+), 537 ([M−H]−). Anal. calcd for C27H42N2O5S2: C, 60.19; H, 7.86; N, 5.20. Found: C, 60.28, H, 7.93; N, 5.13.

Provenance & Evidence