(Trifluoromethyl)trimethylsilane → 8-(2-Chloro-benzenesulfonyl)-2-[4-(2,2,2-trifluoro-1-hydroxy-1-methyl-ethyl)-phenyl]-2,8-diaza-spiro[4.5]decan-1-one

HRID 2194138

Reaction equation

HRID 2194138 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:14][CH2:13][C:12]3([CH2:19][CH2:18][N:17]([S:20]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=4[Cl:29])(=[O:22])=[O:21])[CH2:16][CH2:15]3)[C:11]2=[O:30])=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[F:31][C:32]([Si](C)(C)C)([F:34])[F:33].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1.Cl>[Cl:29][C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=1[S:20]([N:17]1[CH2:18][CH2:19][C:12]2([C:11](=[O:30])[N:10]([C:7]3[CH:6]=[CH:5][C:4]([C:1]([OH:3])([CH3:2])[C:32]([F:34])([F:33])[F:31])=[CH:9][CH:8]=3)[CH2:14][CH2:13]2)[CH2:15][CH2:16]1)(=[O:22])=[O:21]

Participants

6

Reactant 3

HCID 552549(Trifluoromethyl)trimethylsilaneHCID 2724141Tetrabutylammonium FluorideHCID 595779632-(4-Acetyl-phenyl)-8-(2-chloro-benzenesulfonyl)-2,8-diaza-spiro[4.5]decan-1-one2×

Product 1

HCID 595780328-(2-Chloro-benzenesulfonyl)-2-[4-(2,2,2-trifluoro-1-hydroxy-1-methyl-ethyl)-phenyl]-2,8-diaza-spiro[4.5]decan-1-oneYield 60.5%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 8028TetrahydrofuranSolvent

Procedure

2-(4-Acetyl-phenyl)-8-(2-chloro-benzenesulfonyl)-2,8-diaza-spiro[4.5]decan-1-one (0.13 g), product of example 151), dissolved in THF (12 ml) under an argon atmosphere was treated at RT with (trifluoromethyl)trimethylsilane (0.062 g) then with tetra-n-butylammonium fluoride (1M solution in THF, 0.29 ml) and the reaction mixture was stirred overnight at RT. The mixture was made acidic with 3M aqueous HCl (a few drops) and stirred further 15 minutes. The solvent was removed in vacuo and the residue adsorbed on silica gel and chromatographed over silica gel (AcOEt/heptane, gradient from 0 to 40%) to give the desired product as white solid (0.091 g). MS (ESI): 517.1 MH+).

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue adsorbed on silica gel and chromatographed over silica gel (AcOEt/heptane, gradient from 0 to 40%)

Sources & evidence

ORD record
ord-0646c067664e4abd8f11a6ac87460ef8
Source dataset
uspto-grants-2012_12
Patent number
US08329904B2

Linked notes

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