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

HRID 1689258Notes

Reaction equation

HRID 1689258 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[Si]([O:26][CH2:27][CH2:28][C:29]1[CH:30]=[C:31]([CH2:34][N:35]2[CH2:53][CH2:52][C:38]3([O:43][CH2:42][CH2:41][N:40]([C:44]([C:46]4[S:47][C:48]([CH3:51])=[CH:49][CH:50]=4)=[O:45])[CH2:39]3)[CH2:37][CH2:36]2)[S:32][CH:33]=1)(C(C)(C)C)(C)C>O1CCCC1>[OH:26][CH2:27][CH2:28][C:29]1[CH:30]=[C:31]([CH2:34][N:35]2[CH2:36][CH2:37][C:38]3([O:43][CH2:42][CH2:41][N:40]([C:44]([C:46]4[S:47][C:48]([CH3:51])=[CH:49][CH:50]=4)=[O:45])[CH2:39]3)[CH2:52][CH2:53]2)[S:32][CH:33]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 57989318(9-((4-(2-(tert-Butyldimethylsilyloxy)ethyl)thiophen-2-yl)methyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)(5-methylthiophen-2-yl)methanone

Product 1

HCID 57989018(9-((4-(2-Hydroxyethyl)thiophen-2-yl)methyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)(5-methylthiophen-2-yl)methanone

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Tetrabutylammonium fluoride (1M in tetrahydrofuran, 2 mL) was added to a solution of (9-((4-(2-(tert-butyldimethylsilyloxy)ethyl)thiophen-2-yl)methyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)(5-methylthiophen-2-yl)methanone (example 27, step c) (0.65 g) in tetrahydrofuran (7 mL). After 1 h, the solution was evaporated in vacuo. Purification by silica gel chromatography, eluting with 20:1 ethyl acetate:triethylamine, gave the subtitled compound as a gum. Yield 0.45 g.

Workup

  1. customthe solution was evaporated in vacuo
  2. customPurification by silica gel chromatography
  3. washeluting with 20:1 ethyl acetate

Sources & evidence

ORD record
ord-a3a8825110714d5cbae448beb599bd3a
Source dataset
uspto-grants-2012_04
Patent number
US08148373B2

Reaction notes

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