Tetrabutylammonium Fluoride → 1-[4-(1-Ethyl-1-{4-[(2-methanesulfonylethylamino)methyl]-3-methylphenyl}propyl)-2-methylphenoxy]-3,3-dimethylbutan-2-ol

HRID 502060Notes

Reaction equation

HRID 502060 reaction equation
[Si]([O:8][CH:9]([C:39]([CH3:42])([CH3:41])[CH3:40])[CH2:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]([C:23]2[CH:36]=[CH:35][C:26]([CH2:27][NH:28][CH2:29][CH2:30][S:31]([CH3:34])(=[O:33])=[O:32])=[C:25]([CH3:37])[CH:24]=2)([CH2:21][CH3:22])[CH2:19][CH3:20])=[CH:14][C:13]=1[CH3:38])(C(C)(C)C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1.O>[CH2:19]([C:18]([C:15]1[CH:16]=[CH:17][C:12]([O:11][CH2:10][CH:9]([OH:8])[C:39]([CH3:40])([CH3:42])[CH3:41])=[C:13]([CH3:38])[CH:14]=1)([C:23]1[CH:36]=[CH:35][C:26]([CH2:27][NH:28][CH2:29][CH2:30][S:31]([CH3:34])(=[O:33])=[O:32])=[C:25]([CH3:37])[CH:24]=1)[CH2:21][CH3:22])[CH3:20]

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 68464086[4-(1-{4-[2-(t-Butyldimethylsilanyloxy)-3,3-dimethylbutoxy]-3-methylphenyl}-1-ethylpropyl)-2-methylbenzyl]-(2-methanesulfonylethyl)amine

Product 1

HCID 100976061-[4-(1-Ethyl-1-{4-[(2-methanesulfonylethylamino)methyl]-3-methylphenyl}propyl)-2-methylphenoxy]-3,3-dimethylbutan-2-olYield 79.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of [4-(1-{4-[2-(t-butyldimethylsilanyloxy)-3,3-dimethylbutoxy]-3-methylphenyl}-1-ethylpropyl)-2-methylbenzyl]-(2-methanesulfonylethyl)amine (1.47 g, 2.43 mmol) in THF (30 mL) is added 1M TBAF (2.7 mL, 2.7 mmol), and refluxed for 2 h. After cooling to RT, the mixture is diluted with H2O (20 mL) and extracted with EtOAc (3×30 mL). The combined organic layers are MgSO4 dried, concentrated, and chromatographed (80% EtOAc/Hex) to give the title compound (0.97 g, 1.93 mmol, 79%).

Workup

  1. temperaturerefluxed for 2 h
  2. extractionextracted with EtOAc (3×30 mL)
  3. customdried
  4. concentrationconcentrated
  5. customchromatographed (80% EtOAc/Hex)

Sources & evidence

ORD record
ord-2874cf4f853b4860a6a4860361ad2a45
Source dataset
uspto-grants-2010_08
Patent number
US07772425B2

Reaction notes

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