Tetrahydrofuran → t-butyl (R)-2-hydroxy-1-(4-((S)-2-methylbutoxy)phenyl)ethylcarbamate

Beteiligte Stoffe

Reaktionsschritte

A room temperature suspension of lithium aluminum hydride (320 mg, 8.5 mmol) and tetrahydrofuran (50 mL) was treated slowly with a solution of (2R)-methyl 2-(tert-butoxycarbonylamino)-(4-((S)-2-methyl-butoxy)-phenyl)acetate and tetrahydrofuran (40 mL). The resulting reaction mixture was maintained 30 min, then treated with ethyl acetate (12 mL) and an aqueous solution of potassium hydroxide (10% wt/wt, 24 mL). The mixture was allowed to stir for 1 h, then dried with MgSO4, filtered and concentrated to afford t-butyl (R)-2-hydroxy-1-(4-((S)-2-methylbutoxy)phenyl)ethylcarbamate (2.2 g, 88% yield) as a yellow solid: 1H NMR (400 MHz, CDCl3) δ 7.22 (d, J=8.6 Hz, 2H), 6.90 (d, J=8.8 Hz, 2H), 5.12 (d, J=6.3 Hz, 1H), 4.74 (br. s., 1H), 3.80-3.87 (m, 3H), 3.74 (dd, J=9.1, 6.6 Hz, 1H), 1.87 (dq, J=13.0, 6.5 Hz, 1H), 1.53-1.64 (m, 2H), 1.45 (s, 9H), 1.22-1.34 (m, 1H), 1.03 (d, J=6.6 Hz, 3H), 0.97 (t, J=7.5 Hz, 3H); LRMS (ESI) m/e 324.1 [(M+H)+, calcd for C18H30NO4 324.4].

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