Tetrahydrofuran → HCID 87571648, compound

HRID 1182860Notes

Reaction equation

HRID 1182860 reaction equation
[C:1]([OH:8])(=[O:7])/[CH:2]=[CH:3]/[C:4]([OH:6])=[O:5].[NH2:9][CH2:10][CH2:11][O:12]/[N:13]=[C:14]1/[C:15]([CH3:37])([CH3:36])[C@@:16]2([OH:35])[C@:29]([CH3:32])([CH2:30][CH2:31]/1)[C@@H:28]1[C@H:19]([C@H:20]3[C@@:24]([CH2:26][CH2:27]1)([CH3:25])[C@@H:23]([OH:33])[CH2:22][CH2:21]3)[CH2:18][C@@H:17]2[OH:34].C1C(=O)N(Br)C(=O)C1.C1COCC1>O1CCOCC1.O.[Cl-].[Na+].O>[C:1]([OH:8])(=[O:7])/[CH:2]=[CH:3]/[C:4]([OH:6])=[O:5].[NH2:9][CH2:10][CH2:11][O:12]/[N:13]=[C:14]1/[C:15]([CH3:37])([CH3:36])[C@@:16]2([OH:35])[C@:29]([CH3:32])([CH2:30][CH2:31]/1)[C@@H:28]1[C@H:19]([C@H:20]3[C@@:24]([CH2:26][CH2:27]1)([CH3:25])[C:23](=[O:33])[CH2:22][CH2:21]3)[CH2:18][C@@H:17]2[OH:34]

Participants

7

Reactant 3

HCID 8028TetrahydrofuranHCID 67184N-bromobutanimideHCID 87572387HCID 87572387, compound

Product 1

HCID 87571648HCID 87571648, compoundYield 55%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 312751,4-DioxaneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a stirred solution of (E)-3-(2-aminoethoxyimino)-4,4-dimethylandrostane-5α,6α,17β-triol (Example 16, 109 mg) in dioxane (3.5 ml) and water (0.4 ml), NBS (112 mg) was added. After 5 h THF (15 ml) and brine (20 ml) were added and the mixture stirred for 10 min. The phases were separated and the aqueous phase was extracted with THF. The combined organic extracts were washed with aqueous NaHSO3, brine, dried over MgSO4, filtered and evaporated to dryness. The crude product was purified by flash chromatography (SiO2, DCM/MeOH/26% NH4OH 90/10/1). To the concentrated fractions a stoichiometric amount of fumaric acid in MeOH was added and evaporated to dryness. The residue was triturated with Et2O for 0.5 h and the precipitate was filtered to give the title compound as a white solid (58 mg, 55%).

Workup

  1. customThe phases were separated
  2. extractionthe aqueous phase was extracted with THF
  3. washThe combined organic extracts were washed with aqueous NaHSO3, brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated to dryness
  7. customThe crude product was purified by flash chromatography (SiO2, DCM/MeOH/26% NH4OH 90/10/1)
  8. additionTo the concentrated fractions a stoichiometric amount of fumaric acid in MeOH was added
  9. customevaporated to dryness
  10. customThe residue was triturated with Et2O for 0.5 h
  11. filtrationthe precipitate was filtered

Sources & evidence

ORD record
ord-01e6633666bd491e8db81a95c0525fa0
Source dataset
uspto-grants-2014_03
Patent number
US08664210B2

Reaction notes

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