Tetrabutylammonium Fluoride → (9-((5-(2-Hydroxyethyl)thiophen-2-yl)methyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)(2-methylthiazol-4-yl)methanone

HRID 470997Notes

Reaction equation

HRID 470997 reaction equation
[Si]([O:8][CH2:9][CH2:10][C:11]1[S:15][C:14]([CH2:16][N:17]2[CH2:35][CH2:34][C:20]3([O:25][CH2:24][CH2:23][N:22]([C:26]([C:28]4[N:29]=[C:30]([CH3:33])[S:31][CH:32]=4)=[O:27])[CH2:21]3)[CH2:19][CH2:18]2)=[CH:13][CH:12]=1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[OH:8][CH2:9][CH2:10][C:11]1[S:15][C:14]([CH2:16][N:17]2[CH2:18][CH2:19][C:20]3([O:25][CH2:24][CH2:23][N:22]([C:26]([C:28]4[N:29]=[C:30]([CH3:33])[S:31][CH:32]=4)=[O:27])[CH2:21]3)[CH2:34][CH2:35]2)=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 57989061(9-((5-(2-(tert-Butyldimethylsilyloxy)ethyl)thiophen-2-yl)methyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)(2-methylthiazol-4-yl)methanone

Product 1

HCID 57989315(9-((5-(2-Hydroxyethyl)thiophen-2-yl)methyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)(2-methylthiazol-4-yl)methanone

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of (9-((5-(2-(tert-butyldimethylsilyloxy)ethyl)thiophen-2-yl)methyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)(2-methylthiazol-4-yl)methanone (example 14, step b) (0.3 g) in THF (5 mL) was treated dropwise with a solution of tetrabutylammonium fluoride (1M in THF, 0.672 mL). The mixture was allowed to stand at 20° C. for 30 minutes. The solvents were evaporated using a stream of nitrogen and the residue was purified by flash silica chromatography, elution gradient 1% triethylamine and 2.5% methanol in dichloromethane. Pure fractions were evaporated to dryness to afford the subtitled compound. Yield 0.187 g.

Workup

  1. customThe solvents were evaporated
  2. customthe residue was purified by flash silica chromatography, elution gradient 1% triethylamine and 2.5% methanol in dichloromethane
  3. customPure fractions were evaporated to dryness

Sources & evidence

ORD record
ord-0dfb83260a1f4a0db39adfe34c1b8df4
Source dataset
uspto-grants-2014_01
Patent number
US08629271B2

Reaction notes

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