Tetrahydrofuran → [5-(4-Methyl-5-trifluoromethyl-isoxazol-3-yl)-thiophen-2-yl]-((S)-2-pyrrolidin-1-ylmethyl-pyrrolidin-1-yl)-methanone

Participants

Reaction Steps

Prepared from 5-(4-Methyl-5-trifluoromethyl-isoxazol-3-yl)-thiophene-2-carboxylic acid and (S)-(+)-1-(2-pyrrolidinylmethyl)-pyrrolidine by the method described in Example 2 Method B reversing the order of addition such that solid acid chloride was added to a THF solution of triethylamine and piperidine derivative. The reaction mixture was evaporated to a solid, triturated and filtered with the aid of water, then washed with a saturated aqueous NaHCO3 solution followed by water to afford product as a pale yellow solid (88 mg, 85%). 1H NMR (CDCl3) 1.76 (m, 4H), 1.96-2.10 (m, 4H), 2.37 (d, J=1.3, 3H), 2.56-2.64 (m, 6H), 3.80 (m, 2H), 4.48 (m, 1H), 7.50 (d, J=4.0, 1H), 7.57 (br, 1H). 19F NMR −63.2. LC/MS 4.66 min, [M+1]+ 414.

Provenance & Evidence