HCID 118572841, compound → HCID 118572837, compound

HRID 59054Notes

Reaction equation

HRID 59054 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]=[C:25]2[Cl:33])[CH2:6]1)(=[O:3])[CH3:2]>C1(C)C=CC=CC=1>[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]=[C:25]2[Cl:33])[CH2:6]1)(=[O:3])[CH3:2]

Participants

3

Reactant 1

HCID 118572841HCID 118572841, compound

Product 1

HCID 118572837HCID 118572837, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 3β-Acetoxy-17-(2-chlorobenzimidazol-1-yl)-16-formylandrosta-5,16-diene (22a), (0.15 g, 0.304 mmol) in dry toluene (3 mL) was refluxed in the presence of chlorotris (triphenylphosphine) rhodium (I) (0.29 g, 0.311 mmol) for 60 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 (8:2)] to give 0.04 g (28%) of pure 22b: mp 161-165° C.; IR (Neat) 2926, 2853, 1629, 1403, 1462, 1369, 1233, 1035, 847 cm−1; 1H NMR (500 MHz, CDCl3) δ1.05 (d, 6H, 18 and 19-CH3), 2.04 (s, 3H, 3β-OCOCH3), 4.62 (m, 1H, 3α-H), 5.44 (m, 1H, 6-H), 6.06 (s, 1H, 16-H), 7.33 (m, 1H, aromatic-H), 7.52 (m, 1H, aromatic-H), and 7.68 (m, 2H, aromatic-H).

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 (8:2)]

Sources & evidence

ORD record
ord-bb875dd8b2844d4ba093966619593916
Source dataset
uspto-grants-2016_09
Patent number
US09439912B2

Reaction notes

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