Tetrabutylammonium Fluoride → 2,2,2-Trifluoro-1-(9-(2-fluoro-5-(2-hydroxyethyl)benzyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)ethanone

HRID 446466Notes

Reaction equation

HRID 446466 reaction equation
CCCC[N+](CCCC)(CCCC)CCCC.[F-].[Si]([O:26][CH2:27][CH2:28][C:29]1[CH:30]=[CH:31][C:32]([F:53])=[C:33]([CH:52]=1)[CH2:34][N:35]1[CH2:51][CH2:50][C:38]2([O:43][CH2:42][CH2:41][N:40]([C:44](=[O:49])[C:45]([F:48])([F:47])[F:46])[CH2:39]2)[CH2:37][CH2:36]1)(C(C)(C)C)(C)C>C1COCC1>[F:48][C:45]([F:46])([F:47])[C:44]([N:40]1[CH2:39][C:38]2([CH2:50][CH2:51][N:35]([CH2:34][C:33]3[CH:52]=[C:29]([CH2:28][CH2:27][OH:26])[CH:30]=[CH:31][C:32]=3[F:53])[CH2:36][CH2:37]2)[O:43][CH2:42][CH2:41]1)=[O:49]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 581685901-(9-(5-(2-(Tert-butyldimethylsilyloxy)ethyl)-2-fluorobenzyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)-2,2,2-trifluoroethanone

Product 1

HCID 581685882,2,2-Trifluoro-1-(9-(2-fluoro-5-(2-hydroxyethyl)benzyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)ethanone

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

TBAF (1M in THF, 16.4 mL) was added to a solution of 1-(9-(5-(2-(tert-butyldimethylsilyloxy)ethyl)-2-fluorobenzyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)-2,2,2-trifluoroethanone [Example 44, step a] (8.5 g) in THF (100 mL) and the resultant solution allowed to stand at 20° C. for 18 hours. The solvent was evaporated under reduced pressure and the residue was purified by flash silica chromatography, using 2% methanol in dichloromethane containing 1% triethylamine as solvent. Fractions containing the product were evaporated to dryness to afford the subtitled compound. Yield 4.2 g. m/z 405 (M+H)+ (APCI).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customthe residue was purified by flash silica chromatography
  3. additionFractions containing the product
  4. customwere evaporated to dryness

Sources & evidence

ORD record
ord-524d3a622d6f4a718951b5db3b241555
Source dataset
uspto-grants-2013_07
Patent number
US08476265B2

Reaction notes

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