Water → HCID 54590989, compound

HRID 2401127Notes

Reaction equation

HRID 2401127 reaction equation
C([Si](C1C=CC=CC=1)(C1C=CC=CC=1)[O:6][CH:7]1[CH2:35][CH2:34][C:10]2([C:14](=[O:15])[N:13]([C:16]3[C:17]([CH3:33])=[N:18][C:19]([N:22]4[CH2:26][CH2:25][C@@H:24]([N:27]5[CH2:31][CH2:30][CH2:29][C@@H:28]5[CH3:32])[CH2:23]4)=[CH:20][CH:21]=3)[CH2:12][CH2:11]2)[CH2:9][CH2:8]1)(C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O>O1CCCC1>[OH:6][CH:7]1[CH2:8][CH2:9][C:10]2([C:14](=[O:15])[N:13]([C:16]3[C:17]([CH3:33])=[N:18][C:19]([N:22]4[CH2:26][CH2:25][C@@H:24]([N:27]5[CH2:31][CH2:30][CH2:29][C@@H:28]5[CH3:32])[CH2:23]4)=[CH:20][CH:21]=3)[CH2:12][CH2:11]2)[CH2:34][CH2:35]1

Participants

5

Reactant 3

HCID 962WaterHCID 2724141Tetrabutylammonium Fluoride2×HCID 71280567HCID 71280567, compound

Product 1

HCID 54590989HCID 54590989, compoundYield 29.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To a solution of 8-(tert-butyl-diphenyl-silanyloxy)-2-[2-methyl-6-((2S,3′R)-2-methyl-[1,3′]bipyrrolidinyl-1′-yl)-pyridin-3-yl]-2-aza-spiro[4.5]decan-1-one (89 mg, 0.14 mmol) in tetrahydrofuran (2 mL) was added 1 M solution of tetrabutylammoniumfluoride in tetrahydrofuran (0.15 mL, 0.15 mmol). The resulting mixture was stirred for 24 hours at ambient temperature and then added additional 1 M solution of tetrabutylammoniumfluoride in tetrahydrofuran (0.15 mL, 0.15 mmol). The resulting mixture was heated to 70° C. for 30 hours then allowed the mixture to cool to ambient temperature. Water (10 mL) was added to the reaction mixture, extracted with EtOAc (2×10 mL). The combined organic extracts were dried over Na2SO4, filtered and concentrated to afford a crude solid which was then purified by flash column chromatography (5% 7N NH3 in MeOH/CH2Cl2) to provide 17 mg (29% yield) of the title compound as a solid.

Workup

  1. temperatureThe resulting mixture was heated to 70° C. for 30 hours
  2. temperatureto cool to ambient temperature
  3. extractionextracted with EtOAc (2×10 mL)
  4. dry with materialThe combined organic extracts were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto afford a crude solid which
  8. customwas then purified by flash column chromatography (5% 7N NH3 in MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-028e850a51aa4b378e61f558ba8e1747
Source dataset
uspto-grants-2014_08
Patent number
US08796278B2

Reaction notes

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