HCID 10595960, compound → HCID 11002256, compound

HRID 1604294Notes

Reaction equation

HRID 1604294 reaction equation
C([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[CH:28]=[CH:27][N:26]=[CH:25]2)[CH2:6]1)(=O)C>CO.[OH-].[K+]>[OH: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[CH:28]=[CH:27][N:26]=[CH:25]2)[CH2:6]1

Participants

4

Reactant 1

HCID 10595960HCID 10595960, compound2×

Product 1

HCID 11002256HCID 11002256, compoundYield 96.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14797Potassium HydroxideSolvent

Procedure

The method followed that described in Synthesis Example 4, but using 3β-acetoxy-17-(1H-imidazol-1-yl)-androsta-5,16-diene (Compound 10) (2.72 g, 7.16 mmol) in methanol (30 ml), 10% methanolic KOH (17 ml), and the mixture was stirred at room temp under N2 for 2 h. Following the conentional workup gave rise to Compound 11 (2.34 g, 95%), mp 220-223° C. 1H NMR (300 MHz, CDCl3): δ 1.01 (3H, s, 18-Me), 1.06 (3H, s, 19-Me), 3.53 (1H, m, 3α-H), 5.39 (1H, d, J=5 Hz, 6-H), 5.69 (1H, s, 16-H), 7.08 (2H, br. s, 4' and 5'-H), and 7.64 (1H, s, 2'-H). Analysis calculated for C25H30ON2 : C, 78.05; H, 8.94; N, 8.28; Found: C, 78.02; H, 9.00; N, 8.22. HRMS calcd. for C22H30ON2 338.2358, found 338.2361.

Workup

  1. customthat described in Synthesis Example 4

Sources & evidence

ORD record
ord-8c3e18667a3f4084bc7f4b83cc00a6fc
Source dataset
uspto-grants-1999_11
Patent number
US05994335

Reaction notes

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