Sodium Bicarbonate → tert-butyl (2S,3R)-4-(3-(allyloxy)-1-(3-methoxyphenyl)propylamino)-3-hydroxy-1-phenylbutan-2-ylcarbamate

Participants

Reaction Conditions

Reaction Steps

Step R (4): Lithium perchlorate (936 mg, 8.80 mmol) was added to a mixture of 3-(allyloxy)-1-(3-methoxyphenyl)propan-1-amine (390 mg, 1.76 mmol) from Step R(3) and tert-butyl (S)-1-((S)-oxiran-2-yl)-2-phenylethylcarbamate (464 mg, 1.76 mmol) from Aldrich, dissolved in CH3CN (10 mL). The resulting mixture was heated at 50° C. for 16 h. The reaction mixture was poured into a mixture of brine and saturated aqueous NaHCO3 solution. Extracted with EtOAc, washed combined extracts with brine, dried over Na2SO4, filtered, and concentrated. The residue was purified by silica gel chromatography to give 700 mg (quantitative yield) of tert-butyl (2S,3R)-4-(3-(allyloxy)-1-(3-methoxyphenyl)propylamino)-3-hydroxy-1-phenylbutan-2-ylcarbamate as a mixture of two diastereomers. LC-MS (M+H)+=485.57; 1H NMR (300 MHz, CDCl3) δ ppm 1.14-1.43 (m, 9H) 2.56-3.04 (m, 4H) 3.24-3.38 (m, 1H) 3.39-3.58 (m, 2H) 3.69-4.01 (m, 7H) 4.60 (t, J=9.88 Hz, 1H) 5.04-5.30 (m, 2H) 5.72-5.99 (m, 1H) 6.73-7.00 (m, 2H) 7.09-7.33 (m, 7H).

Provenance & Evidence