2,2,2-trifluoro-N-((1S,3R)-3-hydroxy-6-isopropoxy-2,3-dihydro-1H-inden-1-yl)acetamide → (S)-methyl 2-(benzyloxycarbonylamino)-3-(3,5-dichlorophenyl)propanoate

Participants

Reaction Steps

Step BF (2): To a solution of (Z)-methyl 2-(benzyloxycarbonylamino)-3-(3,5-dichlorophenyl)acrylate (46.08 g, 121.3 mmol) in methylene chloride (435 mL) was added (+)-1,2-bis((2S,5S)-2,5-Diethylphospholano)benzene(cyclooctadiene)Rhodium(I) trifluoromethanesulfonate (4.02 g, 6.08 mmol). The solution was split between two Parr bottles and shaken under 50 psi hydrogen for 8 h. The combined reactions were concentrated in vacuo and subjected to silica gel chromatography (25% EtOAc/hexane) to yield (S)-methyl 2-(benzyloxycarbonylamino)-3-(3,5-dichlorophenyl)propanoate (40.94 g, 88% yield). 1H NMR (500 MHz, CDCl3) δ 7.28-7.39 (m, 5H) 7.24 (d, J=7.02 Hz, 1H) 7.00 (s, J=1.53 Hz, 2H) 5.34 (d, J=7.63 Hz, 1H) 5.10 (q, J=12.21 Hz, 2H) 4.58-4.68 (m, 1H) 3.73 (s, 3H) 3.05-3.15 (m, 1H) 2.95-3.05 (m, 1H).

Provenance & Evidence