1-(4-CHLORO-PHENYL)-CYCLOPROPYLAMINE

To a stirred solution of 4-methoxybenzyl (1 -(4-chlorophenyl)cyclopropyl)carbamate (step 3, 25.0 g, 75.52 mmol, 1.0 eq) in DCM (200 ml) was added TFA (50 ml). The reaction mixture was stirred at room temperature for overnight. TLC indicated starting material wasconsumed and the desired product was observed. The reaction mixture was evaporated under reduced pressure, cooled to 0 C, pH adjusted to 8.0 with 5% NaHCO3 solution and extracted with DCM (3x250 ml). The combined organic extracts were washed with water (250 ml), dried over sodium sulfate, filtered and evaporated under reduced pressure. The residue was purified by silicagel column chromatography by using 10% MeOH in DCM as an eluent toobtain the compound as a brown color liquid. To this liquid compound, methanol (100 ml) was added and stirred at room temperature for about 1 hour. The solid formed was removedby filtration and the filtrate was evaporated under reduced pressure to obtain the desired product (7.0 g, 55.5% yield) as colourless oil. 'H NMR (300 MHz, DMSO-d6): ppm 7.35- 7.26 (m, 4H), 2.33 (br.s., 2H), 1.0-0.94 (m, 2H), 0.92-0.86 (m, 2H); ESI-MS: mlz 168.01 (M+H)tTo a stirred solution of 1 -benzyl 3 -((3aR , 5aR , 5bR , 7aR , 95, 11 aR, 1 ibR, 1 3a5)-3a-iso cyanato- 1 -isopropyl-5a, 5b, 8, 8, 11 a-pentamethyl-2-oxo-3 , 3a, 4, 5, 5a, 5b, 6, 7, 7a, 8, 9, 10, 11, 11 a, 1 ib, 12, 13, 1 3a-octadecahydro-2H-cyclopenta[ajchrysen-9-yl) (1R, 35)-2, 2-dimethylcyclo butane-i, 3-dicarboxylate (Intennediate-2, 3.0 g, 4.213 mmol, 1.0 eq) in THF (30 ml) wasadded DIPEA (2.16 ml, 12.64 mmol, 3.0 eq) followed by i-(4-chlorophenyl)cyclopropan-i- amine (Intennediate-4, 0.847 g, 5.056 mmol, 1.2 eq). The reaction mixture was stirred at room temperature for about 16 hours. TLC indicated starting material was consumed and the desired product was observed. The reaction mixture was diluted with water (75 ml) andextracted with ethyl acetate (3x75 ml). The combined organic extracts were washed with water (75 ml) and brine solution (50 ml). The organic layer was dried over sodium sulfate, filtered and evaporated under reduced pressure. The residue was purified by silicagel column chromatography by using 0-2% methanol in dichloromethane gradient. The fractionscontaining the expected product were combined and concentrated under reduced pressure to give the desired product (3.0 g, 80.9% yield) as a white solid. 'H NMR (300 MHz, CDC13): ppm 7.37-7.34 (m, 5H), 7.30 (d, J = 8.7 Hz, 2H), 7.13 (d, J = 8.7 Hz, 2H), 5.16, 5.10 (ABq, JAB= 12.3 Hz, 2H), 5.09 (s, 1H), 4.76 (s, 1H), 4.44 (dd, J= 11.4, 4.8 Hz, 1H), 3.18-3.07 (m, 1H), 2.87-2.57 (m, 5H), 2.20 (d, J = 18.3 Hz, 1H), 2.14-1.98 (m, 2H), 1.91-1.80 (m, 2H), 1.80-1.61 (m, 4H), 1.56-1.39 (m, 4H), 1.39-1.25 (m, 6H), 1.34 (s, 3H), 1.22 (s, 3H), 1.19 (s, 3H), 1.17-1.0 (m, 4H), 0.97 (s, 3H), 0.91 (s, 3H), 0.88 (s, 3H), 0.85 (s, 6H), 0.79 (m, 1H), 0.75 (s, 3H); ESI-MS: mlz 901.46 (M+Na)t

Molecular Weight:167.63
XLogP3:1.8
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:1
Exact Mass:167.0501770
Monoisotopic Mass:167.0501770
Topological Polar Surface Area:26
Heavy Atom Count:11
Complexity:146
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes