(R)-(4-biphenylcarbonylamino)-2(R)-hydroxy-6-nitroindane → (R)-(4-biphenylcarbonylamino)-2(R)-hydroxy-6-aminoindane

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Reaction Steps

Combine 1 (R)-(4-biphenylcarbonylamino)-2(R)-hydroxy-6-nitroindane 55.7 g, 550 mL of DMF and 2.8 g of 10% Pd/C catalyst. Hydrogenate at 50 psi (345 kPa) of hydrogen at ambient temperature for 4.75 h. Filter the reaction mixture and dilute the filtrate with 1200 mL of water to give a slurry. Stir the slurry for 30 minutes, filter, wash with water, and dry in vacuo at 50° C. Combine the dried product and about 1 L of water and slurry for 30 minutes, filter, wash with water, and dry in vacuo at 50° C. to afford 45.4 g (90%) of 1 (R)-(4-biphenylcarbonylamino)-2(R)-hydroxy-6-aminoindane: 1R (KBr, cm−1); 3584, 3364, 3277, 1632, 1543, 1326, 1073, 743; HRMS calc'd for C22H20N2O2: 344,4120; Found: 344,1525.

Provenance & Evidence