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

HRID 1689324Notes

Reaction equation

HRID 1689324 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[CH2:57][CH2:56][C:38]3([O:43][CH2:42][CH2:41][N:40]([C:44]([C:46]4[CH:47]=[CH:48][C:49]5[S:53][C:52]([CH3:54])=[N:51][C:50]=5[CH:55]=4)=[O:45])[CH2:39]3)[CH2:37][CH2:36]2)[S:32][CH:33]=1)(C(C)(C)C)(C)C>C1COCC1>[OH:26][CH2:27][CH2:28][C:29]1[CH:30]=[C:31]([CH2:34][N:35]2[CH2:57][CH2:56][C:38]3([O:43][CH2:42][CH2:41][N:40]([C:44]([C:46]4[CH:47]=[CH:48][C:49]5[S:53][C:52]([CH3:54])=[N:51][C:50]=5[CH:55]=4)=[O:45])[CH2:39]3)[CH2:37][CH2:36]2)[S:32][CH:33]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 57989353(9-((4-(2-(Tert-butyldimethylsilyloxy)ethyl)thiophen-2-yl)methyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)(2-methylbenzo[d]thiazol-5-yl)methanone

Product 1

HCID 57989243(9-((4-(2-Hydroxyethyl)thiophen-2-yl)methyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)(2-methylbenzo[d]thiazol-5-yl)methanone

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

TBAF (1M solution in THF, 1.5 mL) was added to stirred solution of (9-((4-(2-(tert-butyldimethylsilyloxy)ethyl)thiophen-2-yl)methyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)(2-methylbenzo[d]thiazol-5-yl)methanone (example 49, step a) (0.36 g) in THF (2 mL). After 1 h, the reaction was evaporated to a gum. Purification by silica gel chromatography eluting with ethyl acetate:triethylamine, 20:1 gave the subtitled compound as a gum. Yield 0.2 g.

Workup

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

Sources & evidence

ORD record
ord-95b58c13802040aa93733587dc0f3b27
Source dataset
uspto-grants-2012_04
Patent number
US08148373B2

Reaction notes

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