Water → Ethynyl-(4-morpholin-4-yl-phenyl)-carbamic acid t-butyl ester

HRID 623673Notes

Reaction equation

HRID 623673 reaction equation
CCCC[N+](CCCC)(CCCC)CCCC.[F-].[C:19]([O:23][C:24](=[O:50])[N:25]([C:38]1[CH:43]=[CH:42][C:41]([N:44]2[CH2:49][CH2:48][O:47][CH2:46][CH2:45]2)=[CH:40][CH:39]=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:50])[N:25]([C:26]#[CH:27])[C:38]1[CH:39]=[CH:40][C:41]([N:44]2[CH2:45][CH2:46][O:47][CH2:48][CH2:49]2)=[CH:42][CH:43]=1)([CH3:22])([CH3:21])[CH3:20]

Participants

5

Reactant 3

HCID 962WaterHCID 2724141Tetrabutylammonium FluorideHCID 131735184(4-Morpholin-4-yl-phenyl)-[(triisopropylsilanyl)-ethynyl]-carbamic acid tert-butyl ester

Product 1

HCID 67985290Ethynyl-(4-morpholin-4-yl-phenyl)-carbamic acid t-butyl esterYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

TBAF (954 mg, 3.02 mmol) was added to a solution of (4-morpholin-4-yl-phenyl)-[(triisopropylsilanyl)-ethynyl]-carbamic acid tert-butyl ester (600 mg, 1.31 mmol) in THF (10 ml) at 0° C. The mixture was stirred for 1 hour at this temperature and was then warmed up 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 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-a51319eb194544e4af6f9fd3f48ab8a9
Source dataset
uspto-grants-2016_04
Patent number
US09302998B2

Reaction notes

Loading…