Water → HCID 9802564, compound

HRID 1735149Notes

Reaction equation

HRID 1735149 reaction equation
[OH:1][C@H:2]1[CH2:7][CH2:6][C@H:5]2[C@H:8]3[C@H:18]([CH2:19][CH2:20][C@:3]12[CH3:4])[C@:16]1([CH3:17])[C@H:11]([N:12]([CH3:22])[C:13](=[O:21])[CH2:14][CH2:15]1)[CH2:10][CH2:9]3.[N+:23]([C:26]1[CH:31]=[CH:30][C:29](F)=[CH:28][CH:27]=1)([O-:25])=[O:24].O>CN(C=O)C>[N+:23]([C:26]1[CH:31]=[CH:30][C:29]([O:1][C@H:2]2[CH2:7][CH2:6][C@H:5]3[C@H:8]4[C@H:18]([CH2:19][CH2:20][C@:3]23[CH3:4])[C@:16]2([CH3:17])[C@H:11]([N:12]([CH3:22])[C:13](=[O:21])[CH2:14][CH2:15]2)[CH2:10][CH2:9]4)=[CH:28][CH:27]=1)([O-:25])=[O:24]

Participants

5

Reactant 3

HCID 962WaterHCID 9590p-FluoronitrobenzeneHCID 10171822HCID 10171822, compound

Product 1

HCID 9802564HCID 9802564, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 17β-hydroxy4-methyl-5α-4-azaandrostan-3-one (1.07 g, 3.5 mmole) and p-nitrofluorobenzene (2.0 ml, 18 mmole) in DMF (15 ml) under N2 was added 95% Nail (180 mg, 7 mmole) in two portions during 10 mins. The mixture was stirred for 3 hours at room temperature and poured onto ice (50 g) and water (50 ml). The mixture was extracted with CH2Cl2 (30 ml×2). The organic layer was washed with brine and dried (Na2SO4). Removal of solvent gave the crude product which was purified via a flash silica gel column eluting with 1:1 ethyl acetate --CH2Cl2 to give the desired title product. Mp. 183°-184° C. (recrystallized from CH2Cl2 -hexane).

Workup

  1. extractionThe mixture was extracted with CH2Cl2 (30 ml×2)
  2. washThe organic layer was washed with brine
  3. dry with materialdried (Na2SO4)
  4. customRemoval of solvent
  5. customgave the crude product which
  6. customwas purified via a flash silica gel column
  7. washeluting with 1:1 ethyl acetate

Sources & evidence

ORD record
ord-e59f01fac0c44f3981a9b71f388c5083
Source dataset
uspto-grants-1996_07
Patent number
US05536727

Reaction notes

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