Tetrabutylammonium Fluoride → (2-Butylthiazol-4-yl)(9-(2-fluoro-3-(2-hydroxyethyl)benzyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)methanone

HRID 1689407Notes

Reaction equation

HRID 1689407 reaction equation
CCCC[N+](CCCC)(CCCC)CCCC.[F-].[Si]([O:26][CH2:27][CH2:28][C:29]1[C:30]([F:58])=[C:31]([CH:55]=[CH:56][CH:57]=1)[CH2:32][N:33]1[CH2:54][CH2:53][C:36]2([O:41][CH2:40][CH2:39][N:38]([C:42]([C:44]3[N:45]=[C:46]([CH2:49][CH2:50][CH2:51][CH3:52])[S:47][CH:48]=3)=[O:43])[CH2:37]2)[CH2:35][CH2:34]1)(C(C)(C)C)(C)C>C1COCC1>[CH2:49]([C:46]1[S:47][CH:48]=[C:44]([C:42]([N:38]2[CH2:37][C:36]3([CH2:53][CH2:54][N:33]([CH2:32][C:31]4[CH:55]=[CH:56][CH:57]=[C:29]([CH2:28][CH2:27][OH:26])[C:30]=4[F:58])[CH2:34][CH2:35]3)[O:41][CH2:40][CH2:39]2)=[O:43])[N:45]=1)[CH2:50][CH2:51][CH3:52]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 57989198(9-(3-(2-(tert-Butyldimethylsilyloxy)ethyl)-2-fluorobenzyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)(2-butylthiazol-4-yl)methanone

Product 1

HCID 57989168(2-Butylthiazol-4-yl)(9-(2-fluoro-3-(2-hydroxyethyl)benzyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)methanone

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

TBAF (1M solution in THF, 2.0 mL) was added to a solution of (9-(3-(2-(tert-butyldimethylsilyloxy)ethyl)-2-fluorobenzyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)(2-butylthiazol-4-yl)methanone (example 78, step h) (0.350 g) in THF (4 mL). After 0.5 h, the solution was concentrated. Purification by silica gel chromatography eluting with 10:1 ethyl acetate; triethylamine gave the subtitled compound as a gum. Yield 0.24 g.

Workup

  1. concentrationthe solution was concentrated
  2. customPurification by silica gel chromatography
  3. washeluting with 10:1 ethyl acetate

Sources & evidence

ORD record
ord-0ca66f8c9d6a45939378b63808b78646
Source dataset
uspto-grants-2012_04
Patent number
US08148373B2

Reaction notes

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