Tetrabutylammonium Fluoride → HCID 70146720, compound

HRID 840180Notes

Reaction equation

HRID 840180 reaction equation
C[Si](C)(C)[O:3][C@H:4]1[CH2:9][CH2:8][C@H:7]2[C@H:10]3[C@H:20]([CH2:21][CH2:22][C@:5]12[CH3:6])[C@:18]1([CH3:19])[C:13]([N:14]([Si:24]([CH3:27])([CH3:26])[CH3:25])[C:15](=[O:23])[CH2:16][CH2:17]1)=[CH:12][C:11]3=[CH:28][C:29]([O:31][CH2:32][CH3:33])=[O:30].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1.CCOC(C)=O>[OH:3][C@H:4]1[CH2:9][CH2:8][C@H:7]2[C@H:10]3[C@H:20]([CH2:21][CH2:22][C@:5]12[CH3:6])[C@:18]1([CH3:19])[C:13]([N:14]([Si:24]([CH3:26])([CH3:25])[CH3:27])[C:15](=[O:23])[CH2:16][CH2:17]1)=[CH:12][C:11]3=[CH:28][C:29]([O:31][CH2:32][CH3:33])=[O:30]

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 70147093HCID 70147093, compound

Product 1

HCID 70146720HCID 70146720, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

The diene disilane prepared above is redissolved in THF (300 mL) and treated with tetrabutylammonium fluoride (1.0 M in THF; 35.0 mL, 35.0 mmole). The desilylation reaction occurs over 20 minutes with stirring at ambient temperature. The reaction mixture is then diluted with EtOAc (500 mL) and washed with brine (3×400 mL). The crude product solution is dried over MgSO4, filtered and evaporated to dryness. The crude product is purified by flash chromatography (1:1 EtOAc/CH2Cl2) to afford 17β-hydroxy-4-trimethylsilyl-7-ethyloxycarbonylmethylene-4-aza-androst-5-en-3-one as a mixture of the E and Z isomers (diolefin). The diolefin is then hydrogenated in a manner similar to that described in Example 7H to give 7β-ethoxycarbonylmethyl-17β-hydroxy-4-aza-5α-androstan-3-one. The compound has the following structure:

Workup

  1. customThe desilylation reaction
  2. washwashed with brine (3×400 mL)
  3. dry with materialThe crude product solution is dried over MgSO4
  4. filtrationfiltered
  5. customevaporated to dryness
  6. customThe crude product is purified by flash chromatography (1:1 EtOAc/CH2Cl2)

Sources & evidence

ORD record
ord-9300a65602e443b9b153915c1eeec0e5
Source dataset
uspto-grants-2002_04
Patent number
US06365597B1

Reaction notes

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