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 1255346Notes

Reaction equation

HRID 1255346 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.

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-88c4fec604ac47ab8e7ead698c05045b
Source dataset
uspto-grants-2013_06
Patent number
US08455483B2

Reaction notes

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