Pivaloyl chloride → HCID 10289703, compound

HRID 2055049Notes

Reaction equation

HRID 2055049 reaction equation
CCCC[N+:5]([CH2:14][CH2:15]CC)([CH2:10][CH2:11][CH2:12][CH3:13])[CH2:6]CCC.[F-].C([Si](C)(C)[O:24][C:25]1[CH:26]=[CH:27][C:28]2[C:29]3[CH:42]([C:43]4[CH:57]=[CH:56][C:46]([O:47]CCN5CCCCC5)=[CH:45][CH:44]=4)[O:41][C:40]4[CH:39]=[C:38]([O:58][Si](C(C)(C)C)(C)C)[CH:37]=[CH:36][C:35]=4[C:30]=3[CH2:31][O:32][C:33]=2[CH:34]=1)(C)(C)C.[CH3:68][C:69]([CH3:74])([CH3:73])[C:70](Cl)=[O:71]>C1COCC1.C(OCC)(=O)C>[OH:24][C:25]1[CH:26]=[CH:27][C:28]2[C:29]3[CH:42]([C:43]4[CH:44]=[CH:45][C:46]([O:47][CH2:15][CH2:14][N:5]5[CH2:6][CH2:13][CH2:12][CH2:11][CH2:10]5)=[CH:56][CH:57]=4)[O:41][C:40]4[CH:39]=[C:38]([O:58][C:70](=[O:71])[C:69]([CH3:74])([CH3:73])[CH3:68])[CH:37]=[CH:36][C:35]=4[C:30]=3[CH2:31][O:32][C:33]=2[CH:34]=1

Participants

6

Reactant 3

HCID 62493Pivaloyl chlorideHCID 2724141Tetrabutylammonium FluorideHCID 115566601-(2-{4-[2,8-Bis-(tert-butyl-dimethyl-silyloxy)-5,11-dihydro-chromeno[4,3-c]-chromen-5-yl]-phenoxy}-ethyl)-piperidine

Product 1

HCID 10289703HCID 10289703, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

TBAF (1 M in THF, 850 μL, 0.85 mmol, 3 eq.) was added drop-wise into a solution of 1-(2-{4-[2,8-Bis-(tert-butyl-dimethyl-silyloxy)-5,11-dihydro-chromeno[4,3-c]chromen-5-yl]-phenoxy}-ethyl)-piperidine (200 mg, 0.285 mmol) in THF (10 mL) at −10° C. The reaction mixture was stirred for 15 minutes. To the reaction mixture was then added 2,2-dimethylpropionic acid chloride (714 μL, 0.285 mmol, 1 eq). The reaction mixture was diluted with ethyl acetate and washed with 5% sodium bicarbonate and then with brine. The organic layer, was dried over anhydrous Na2SO4, and concentrated to yield a crude oil, which was purified by HPLC (using Luna C18 column, 1% TFA in acetonitrile (ACN) and 1% TFA in H2O as gradient solvent system). Two peak were collected separately and evaporated to dryness in vacuum to yield 2,2-Dimethyl-propionic acid 8-hydroxy-11-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-5,11-dihydro-chromeno[4,3-c]chromen-2-yl ester as peak one

Workup

  1. washwashed with 5% sodium bicarbonate
  2. dry with materialThe organic layer, was dried over anhydrous Na2SO4
  3. concentrationconcentrated
  4. customto yield a crude oil, which
  5. customwas purified by HPLC (using Luna C18 column, 1% TFA in acetonitrile (ACN) and 1% TFA in H2O as gradient solvent system)
  6. customTwo peak were collected separately
  7. customevaporated to dryness in vacuum

Sources & evidence

ORD record
ord-ccc4bc659aa94360a84711e698f77a48
Source dataset
uspto-grants-2008_02
Patent number
US07329654B2

Reaction notes

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