Water → t-Butyl ethynyl(4-morpholinobenzyl)carbamate

HRID 623678Notes

Reaction equation

HRID 623678 reaction equation
CCCC[N+](CCCC)(CCCC)CCCC.[F-].[C:19]([O:23][C:24](=[O:51])[N:25]([CH2:38][C:39]1[CH:44]=[CH:43][C:42]([N:45]2[CH2:50][CH2:49][O:48][CH2:47][CH2:46]2)=[CH:41][CH:40]=1)[C:26]#[C:27][Si](C(C)C)(C(C)C)C(C)C)([CH3:22])([CH3:21])[CH3:20].O>C1COCC1>[C:19]([O:23][C:24](=[O:51])[N:25]([C:26]#[CH:27])[CH2:38][C:39]1[CH:44]=[CH:43][C:42]([N:45]2[CH2:46][CH2:47][O:48][CH2:49][CH2:50]2)=[CH:41][CH:40]=1)([CH3:22])([CH3:21])[CH3:20]

Participants

5

Reactant 3

HCID 962WaterHCID 2724141Tetrabutylammonium FluorideHCID 131735187HCID 131735187, compound

Product 1

HCID 117677987t-Butyl ethynyl(4-morpholinobenzyl)carbamateYield 60%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

TBAF (2.18 g, 6.9 mmol) was added to a solution of (4-morpholin-4-yl-benzyl)-[(triisopropylsilanyl)-ethynyl]-carbamic acid t-butyl ester (1.42 g, 3 mmol) in THF (23 ml) at 0° C. The mixture was stirred for 1 hour at this temperature and was then warmed to RT. H2O (15 ml) was added and the organic phase was extracted with Et2O (3×15 ml) and dried over Na2SO4. The solvent was removed under reduced pressure and the desired compound was obtained after purification by column chromatography (PE/AcOEt:80/20 to 75/25). The title compound was obtained as a yellow solid.

Workup

  1. extractionthe organic phase was extracted with Et2O (3×15 ml)
  2. dry with materialdried over Na2SO4
  3. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-fb6d90687a334247b8deacdfa78dabc5
Source dataset
uspto-grants-2016_04
Patent number
US09302998B2

Reaction notes

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