1 in 81% yield (1.8 kg). HPLC Purity: 99.72%, Assay: 98.8% (HPLC, w/w). MS: m/z = 392.7 [M + H]+. IR (KBr) (cm–1): 3047, 2936, 1735, 1244, 1035, 801, 714. 1H NMR (400 MHz, DMSO-d6): δ 8.58 (s, 1 H), 8.43–8.42 (d, 1 H), 7.76–7.74 (d, 1 H), 7.34–7.31 (dd, 1 H), 6.11 (s, 1 H), 5.38 (s, 1 H), 4.44 (m, 1H), 2.19–2.50 (m, 3H), 1.98–2.08 (m, 6H), 1.39–1.85 (m, 9H), 1.03–1.11 (m, 8H). 13C NMR (CDCl3): δ 170.4, 151.6, 147.9, 147.8, 140.0, 133.6, 132.9, 129.1, 122.9, 122.2, 73.8, 57.4, 50.2, 47.3, 38.1, 36.9, 36.7, 35.1, 31.7, 31.4, 30.3, 27.7, 21.4, 20.8, 19.2, 16.5.
Abiraterone (2)
2 (2.88 kg, 72%) as a white solid. HPLC Purity: 99.87%. MS: m/z = 350.3 [M + H]+. IR (KBr) (cm–1): 3236, 3062, 3031, 2931,1596, 1065, 803. 1H NMR (400 MHz, CDCI3): δ 8.61 (s, 1 H), 8.44–8.46 (d, 1 H), 7.63–7.65 (d, 1 H), 7.20–7.23 (dd, 1 H), 5.993–5.996 (d, 1 H), 5.38–5.99 (d, 1 H), 3.48–3.54 (m, 1 H), 2.24–2.32 (m, 3H), 1.97–2.10 (m, 3H), 1.47–1.86 (m, 10H), 1.04–1.10 (s, 8H). 13C NMR (CDCl3): δ 16.58, 19.34, 20.88, 30.45, 31.52, 31.63, 31.81, 35.27, 36.71, 37.20, 42.32, 47.34, 50.37, 57.56, 71.62, 121.28, 123.03, 129.24, 132.99, 133.70, 141.21, 147.79, 147.88, 151.68
see supp info
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PAPER
Improved Procedure for Preparation of Abiraterone Acetate
Chemical Research Division, Ranbaxy Research Laboratory, Gurgaon, Haryana 122001, India
Org. Process Res. Dev., 2014, 18 (4), pp 555–558
DOI: 10.1021/op500044p
*E-mail: Mukesh.madhra@ranbaxy.com. Tel: (91-124)4011832.
