Tetrabutylammonium Fluoride → HCID 15543076, compound

HRID 840178Notes

Reaction equation

HRID 840178 reaction equation
[Si]([O:8][C:9]1[CH:26]=[C:25]2[C@:20]([CH3:28])([CH2:21][CH2:22][C:23](=[O:27])[NH:24]2)[C@@H:19]2[C:10]=1[C@H:11]1[C@@:15]([CH2:17][CH2:18]2)([CH3:16])[C@@H:14]([NH:29][CH:30]2[CH2:32][CH2:31]2)[CH2:13][CH2:12]1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[CH:30]1([NH:29][C@H:14]2[CH2:13][CH2:12][C@H:11]3[C@H:10]4[C@H:19]([CH2:18][CH2:17][C@:15]23[CH3:16])[C@:20]2([CH3:28])[C:25]([NH:24][C:23](=[O:27])[CH2:22][CH2:21]2)=[CH:26][C:9]4=[O:8])[CH2:32][CH2:31]1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 18715533HCID 18715533, compound

Product 1

HCID 15543076HCID 15543076, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

17β-Cyclopropylamino-7-(t-butyldimethylsilyloxy)-4-aza-androst-5,7-dien-3-one (5.000 g, 10.947 mmol) prepared in Example 19B or otherwise obtained is dissolved into THF (50 mL) under nitrogen, and added to this solution is tetrabutylammonium fluoride (1.0 M in THF; 12.00 mL, 12.00 mmol). The reaction mixture is stirred for 90 minutes at ambient temperature, then quenched with water (200 mL). The crude product solution is extracted with EtOAc (2×200 mL), and the combined organic extracts are washed with brine (3×200 mL). The organic solution is dried over MgSO4, filtered and concentrated. The residue is purified by flash chromatography (1:1 EtOAc/CH2Cl2) to give the title compound.

Workup

  1. additionadded to this solution
  2. customquenched with water (200 mL)
  3. extractionThe crude product solution is extracted with EtOAc (2×200 mL)
  4. washthe combined organic extracts are washed with brine (3×200 mL)
  5. dry with materialThe organic solution is dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue is purified by flash chromatography (1:1 EtOAc/CH2Cl2)

Sources & evidence

ORD record
ord-0d3268ecb2d349ecaff738d8e4c76493
Source dataset
uspto-grants-2002_04
Patent number
US06365597B1

Reaction notes

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