p-Toluenesulfonic acid → HCID 57544576, compound

Participants

Reaction Steps

To a solution of (S)-tert-butyl 4-(2-methoxy-2-methylpropyl)-2,2-dimethyl-oxazolidine-3-carboxylate (1.2 g, 3.40 mmol) in MeOH (5 mL) at rt, there was added 4-methylbenzenesulfonic acid (0.65 g, 3.40 mmol). The resulting solution was stirred until no starting material remained (˜1 h). Solvent was removed under vacuum, and the residue was redissolved in acetone (3 mL) and H2O (1 mL). Excess K2CO3 was added to keep the solution basic, followed by (Boc)2O. The mixture was stirred for 20 min, acetone was removed under vacuum, and the aqueous solution was extracted with CH2Cl2 (4×5 mL). After concentration, the residue was purified by flash column chromatography to give (S)-tert-butyl 1-hydroxy-4-methoxy-4-methylpentan-2-ylcarbamate (0.76 g, 78%, 2 steps). 1H NMR (400 MHz, CDCl3): 5.38 (br, 1 H), 3.78 (m, 1 H), 3.66 (m, 1 H), 3.56 (m, 1 H), 3.20 (s, 3 H), 1.66 (m, 2 H), 1.62 (br, 1 H), 1.44 (s, 9 H), 1.20 (s, 6 H); MS m/z 248 (M+H+).

Provenance & Evidence