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

HRID 471275Notes

Reaction equation

HRID 471275 reaction equation
CCCC[N+](CCCC)(CCCC)CCCC.[F-].[Si]([O:26][CH2:27][CH2:28][C:29]1[CH:30]=[C:31]([CH2:34][N:35]2[CH2:51][CH2:50][C:38]3([O:43][CH2:42][CH2:41][N:40]([C:44](=[O:49])[C:45]([F:48])([F:47])[F:46])[CH2:39]3)[CH2:37][CH2:36]2)[S:32][CH:33]=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([CH2:37][CH2:36][N:35]([CH2:34][C:31]3[S:32][CH:33]=[C:29]([CH2:28][CH2:27][OH:26])[CH:30]=3)[CH2:51][CH2:50]2)[O:43][CH2:42][CH2:41]1)=[O:49]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 579892241-(9-((4-(2-(tert-Butyldimethylsilyloxy)ethyl)thiophen-2-yl)methyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)-2,2,2-trifluoroethanone

Product 1

HCID 579890502,2,2-Trifluoro-1-(9-((4-(2-hydroxyethyl)thiophen-2-yl)methyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)ethanone

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

TBAF (1M in THF, 2.96 mL) was added to a stirred solution of 1-(9-((4-(2-(tert-butyldimethylsilyloxy)ethyl)thiophen-2-yl)methyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)-2,2,2-trifluoroethanone (Example 43, step a) (1.500 g, 2.96 mmol) in THF (5 mL). After 1 h, the solution was evaporated to gum. Purification by silica gel chromatography eluting with ethyl acetate:triethylamine, 10:1 gave the subtitled compound as a gum. Yield 0.25 g.

Workup

  1. customthe solution was evaporated to gum
  2. customPurification by silica gel chromatography
  3. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-3848ca79e18a4684bb9c62d2f6df5957
Source dataset
uspto-grants-2014_01
Patent number
US08629271B2

Reaction notes

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