4-Nitrophenol → HCID 21310344, compound

HRID 1837126Notes

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+]>CN(C=O)C.C(#N)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

Conditions

Temperature: 60 °C

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

customThe mixture was partitioned between EtOAc and 1:1 water
washThe organic layer was washed with 2N HCl, water and sat. aq. NaCl
dry with materialdried with Na2SO4
concentrationconcentrated in vacuo
washElution with 20% acetone in hexane

Sources & evidence

ORD record: ord-a0e7bad81bce4181b9ed3f0ba0d17fa4
Source dataset: uspto-grants-2004_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06780853B1

Reaction notes

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