Tetrabutylammonium Fluoride → HCID 67301477, compound

HRID 1014971Notes

Reaction equation

HRID 1014971 reaction equation
[Si]([O:8][C@@H:9]1[C@@:35]2([CH3:36])[C:13](=[CH:14][CH:15]=[C:16]3[C@@H:34]2[CH2:33][CH2:32][C@@:31]2([CH3:37])[C@H:17]3[CH2:18][CH:19]=[C:20]2[C@H:21]([O:23][CH2:24][CH2:25][C:26]([N:28]([CH3:30])[CH3:29])=[O:27])[CH3:22])[CH2:12][C@@H:11]([O:38][Si](C(C)(C)C)(C)C)[CH2:10]1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[OH:8][C@@H:9]1[C@@:35]2([CH3:36])[C:13](=[CH:14][CH:15]=[C:16]3[C@@H:34]2[CH2:33][CH2:32][C@@:31]2([CH3:37])[C@H:17]3[CH2:18][CH:19]=[C:20]2[C@H:21]([O:23][CH2:24][CH2:25][C:26]([N:28]([CH3:29])[CH3:30])=[O:27])[CH3:22])[CH2:12][C@@H:11]([OH:38])[CH2:10]1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 67301392HCID 67301392, compound

Product 1

HCID 67301477HCID 67301477, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

1α,3β-Bis(tert-butyldimethylsilyloxy)-20(R)-(N,N-dimethylaminocarbonylethoxy)pregna-5,7,16-triene (100 mg, 0.15 mmol) was treated with a 1M tetrahydrofuran solution of tetra-n-butylammonium fluoride (1.5 ml) in tetrahydrofuran (6.0 ml) in the same manner as shown in Example 4(2) (at room temperature for 30 minutes and then at 50° C. for 1.5 hours), followed by work up and purification using preparative thin layer chromatography (0.5 mm×2 plates, chloroform:methanol=10:1) to give the titled compound (52 mg, 83.0%) as a colorless foam.

Workup

  1. customat room temperature
  2. customfor 30 minutes
  3. customup and purification

Sources & evidence

ORD record
ord-5d1bab4a22fd4c3996bced023aceddc5
Source dataset
uspto-grants-2011_07
Patent number
US07985744B2

Reaction notes

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