4-Nitrophenol → HCID 21310344, compound

HRID 582522Notes

Reaction equation

HRID 582522 reaction equation
Br[CH2:2][C:3](=[O:25])[C@@H:4]1[C@:21]2([CH3:22])[C@H:7]([C@H:8]3[C@H:18]([CH2:19][CH2:20]2)[C@:16]2([CH3:17])[C@H:11]([CH2:12][C@@:13]([OH:24])([CH3:23])[CH2:14][CH2:15]2)[CH2:10][CH2:9]3)[CH2:6][CH2:5]1.[N+:26]([C:29]1[CH:34]=[CH:33][C:32]([OH:35])=[CH:31][CH:30]=1)([O-:28])=[O:27].C(N(CC)CC)C.[I-].[Na+]>C(#N)C.CN(C=O)C>[OH:24][C@:13]1([CH3:23])[CH2:14][CH2:15][C@@:16]2([CH3:17])[C@@H:11]([CH2:10][CH2:9][C@@H:8]3[C@@H:18]2[CH2:19][CH2:20][C@@:21]2([CH3:22])[C@H:7]3[CH2:6][CH2:5][C@@H:4]2[C:3](=[O:25])[CH2:2][O:35][C:32]2[CH:33]=[CH:34][C:29]([N+:26]([O-:28])=[O:27])=[CH:30][CH:31]=2)[CH2:12]1

Participants

6

Reactant 4

HCID 9804-NitrophenolHCID 5238Sodium IodideHCID 8471TriethylamineHCID 86719952HCID 86719952, compound

Product 1

HCID 21310344HCID 21310344, compoundYield 51.3%

Reagents, catalysts & solvents 1

HCID 21891449acetonitrile N,N-dimethylformamideSolvent

Procedure

A solution of 21-bromo-3α-hydroxy-3β-methyl-5α-pregnan-20-one (250 mg, 0.61 mmol), 4-nitrophenol (127 mg, 0.912 mmol), triethylamine (127 μL,0.912 mmol), and a small amount of sodium iodide in 2:1 acetonitrile DMF was stirred with heating to ~60° C. for 6 hours. The mixture was partitioned between EtOAc and 1:1 water:sat. aq. sodium bicarbonate. The organic layer was washed with 2N HCl, water and sat. aq. NaCl, dried with Na2SO4 and concentrated in vacuo. The crude residue was subjected to flash column chromatography. Elution with 20% acetone in hexane yielded 3α-hydroxy-3β-methyl-21-(4'-nitrophenoxy)-5α-pregnan-20-one (147 mg) as a solid; mp 169-172° C.; TLC Rf (hexane:acetone 4:1)=0.35.

Workup

  1. temperaturewith heating to ~60° C. for 6 hours
  2. customThe mixture was partitioned between EtOAc and 1:1 water
  3. washThe organic layer was washed with 2N HCl, water and sat. aq. NaCl
  4. dry with materialdried with Na2SO4
  5. concentrationconcentrated in vacuo
  6. washElution with 20% acetone in hexane

Sources & evidence

ORD record
ord-f04399fe67f843ef87f9e770e657df01
Source dataset
uspto-grants-1999_07
Patent number
US05925630

Reaction notes

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