Dimethyl Sulfate → HCID 89460106, compound

Participants

Reaction Steps

Tetrabutylammonium iodide (0.110 g, 0.28 mmol), 50% aqueous NaOH (20 mL) and dimethyl sulfate (0.325 mL, 3.41 mmol) were added to a solution of trans-tert-butyl-3-({[tert-butyl(dimethyl)silyl]oxy}methyl)-4-(hydroxymethyl)pyrrolidine-1-carboxylate (0.982 g, 2.84 mmol) in CH2Cl2 (20 mL). The reaction was stirred at rt overnight. TLC showed some starting material remaining so additional dimethyl sulfate (0.150 mL) was added to the reaction mixture and stirred at rt for 3 hrs. Aqueous NH3OH (30 mL) was added to the reaction mixture and stirred at rt for 1 hr. The mixture was diluted with water (20 mL) and extracted with CH2Cl2 (two×30 mL). The organic layer was dried over MgSO4 and concentrated. The residue was purified via flash chromatography eluting with 10% EtOAc/heptane to give the title compound as a colorless oil (451 mg, 44% yield). 1H NMR (400 MHz, chloroform-d) δ ppm 3.60-3.70 (m, 1H), 3.55 (br. s., 2H), 3.37-3.48 (m, 1H), 3.34 (m, 4H), 3.05-3.23 (m, 2H), 2.22-2.40 (m, 1H), 2.07-2.21 (m, 1H), 1.43-1.49 (m, 9H), 0.89 (s, 9H), 0.05 (s, 6H).

Provenance & Evidence