Formic Acid → (R)-tert-Butyl (3-hydroxy-3-phenylpropyl)carbamate

Participants

Reaction Steps

Et3N (2.0 mL, 14.35 mmol) and HCOOH (0.4 mL, 10.60 mmol) were added to a solution of (R)-3-(3-((tert-butoxycarbonyl)amino)-1-hydroxypropyl)phenyl trifluoromethanesulfonate (1.05 g, 2.63 mmol) and Ar was bubbled through the mixture for one minute. 1,3-Bis(diphenylphosphino)propane (1,3-dppp) (0.080 g, 0.194 mmol) and Pd(OAc)2 (0.050 g, 0.223 mmol) were added to the reaction mixture and the later was degassed by applying vacuum/Ar cycle three times. The reaction mixture was heated at +60° C. for 5 h and concentrated under reduced pressure. Aqueous NH4Cl (25%) was added to the residue and the mixture was extracted with MTBE twice. Combined organic layers were washed with brine and concentrated under reduced pressure. Purification by flash chromatography (10%-50% EtOAc-hexanes gradient) gave (R)-tert-butyl (3-hydroxy-3-phenylpropyl)carbamate as a colorless oil. Yield (0.64 g, 97%); 1H NMR (400 MHz, DMSO-d6) δ 7.22-7.30 (m, 4H), 7.14-7.21 (m, 1H), 6.72 (br. t, 1H), 5.14 (d, J=4.4 Hz, 1H), 4.51 (dd, J=6.5, 10.9 Hz, 1H), 2.87-2.98 (m, 2H), 1.60-1.70 (m, 2H), 1.33 (s, 9H).

Provenance & Evidence