HCID 11305671, compound → (3S,8R,9S,10R,13S,14S)-17-(1H-Benzo[D]imidazol-1-YL)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15-dodecahydro-1H-cyclopenta[A]phenanthren-3-YL acetate

HRID 254184Notes

Reaction equation

HRID 254184 reaction equation
[C:1]([O:4][C@H:5]1[CH2:22][CH2:21][C@@:20]2([CH3:23])[C:7](=[CH:8][CH2:9][C@@H:10]3[C@@H:19]2[CH2:18][CH2:17][C@@:15]2([CH3:16])[C@H:11]3[CH2:12][C:13](C=O)=[C:14]2[N:24]2[C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=3[N:26]=[CH:25]2)[CH2:6]1)(=[O:3])[CH3:2]>C(#N)C1C=CC=CC=1.[Pd]>[C:1]([O:4][C@H:5]1[CH2:22][CH2:21][C@@:20]2([CH3:23])[C:7](=[CH:8][CH2:9][C@@H:10]3[C@@H:19]2[CH2:18][CH2:17][C@@:15]2([CH3:16])[C@H:11]3[CH2:12][CH:13]=[C:14]2[N:24]2[C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=3[N:26]=[CH:25]2)[CH2:6]1)(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 11305671HCID 11305671, compound

Product 1

HCID 11464592(3S,8R,9S,10R,13S,14S)-17-(1H-Benzo[D]imidazol-1-YL)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15-dodecahydro-1H-cyclopenta[A]phenanthren-3-YL acetateYield 73.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 7505BenzonitrileSolvent

Procedure

A solution of 3β-Acetoxy-17-(1H-benzimidazol-1-yl)-16-formylandrosta-5,16-diene (3, 2.04 g, 4.45 mmol) in dry benzonitrile (10 mL) was refluxed in the presence of 10% palladium on activated charcoal (1.02 g, i.e., 50% weight of 3) for 5 h. After cooling to room temperature, the catalyst was removed by filtration through a Celite pad. The filtrate was evaporated, and the residue was purified by FCC [petroleum ether/EtOAc/Et3N (7.5:3:0.5)] gave 1.41 g (73.8%) of pure compound 4: mp 159-160° C.; IR(CHCl3) 3687, 2947, 2854, 2358, 2340, 1725, 1633, 1609, 1557, 1489, 1454, 1373, 1291, 1253, 1195, 1136, 1031, 985, 910, 839, 735, 665, 590, 544, 533, 513, 502, 488 cm−1; 1H NMR (300 MHz, CDCl3) δ 1.02 (s, 3H, 18-CH3), 1.07 (s, 3H, 19-CH3), 2.04 (s, 3H, 3β-OCH3), 4.62 (m, 1H, 3α-H), 5.43 (br s, 1H, 6-H), 5.98 (s, 1H, 16-H), 7.30 (m, 2H, aromatic-Hs), 7.49 (s, 1H, aromatic-H), 7.81 (s, 1H, aromatic-H), and 7.95 (s, 1H, 21-H). HRMS calcd 453.2512 (C28H34O2N2.Na+). found 453.2511.

Workup

  1. customthe catalyst was removed by filtration through a Celite pad
  2. customThe filtrate was evaporated
  3. customthe residue was purified by FCC [petroleum ether/EtOAc/Et3N (7.5:3:0.5)]

Sources & evidence

ORD record
ord-069baf88102a449884d84f902cabad4f
Source dataset
uspto-grants-2011_01
Patent number
US07875599B2

Reaction notes

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