Hydrochloric Acid → HCID 178419060, compound

HRID 8774Notes

Reaction equation

HRID 8774 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([CH2:26][CH2:27][O:28][Si](C(C)(C)C)(C)C)([C:14]2[NH:18][N:17]=[C:16]([CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[F-].C([N+](CCCC)(CCCC)CCCC)CCC.Cl>C1COCC1.C(OCC)(=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([CH2:26][CH2:27][OH:28])([C:14]2[NH:18][N:17]=[C:16]([CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:3])([CH3:4])[CH3:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 2724141Tetrabutylammonium FluorideHCID 178418701HCID 178418701, compound

Product 1

HCID 178419060HCID 178419060, compoundYield 66.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1-(tert-butoxycarbonyl)-4-(2-tert-butyldimethylsilyloxyeth-1-yl)-4-(3-benzyl-(1H)-pyrazol-5-yl)piperidine (243 mg, 0.49 mmol) from Step H in THF (5 mL) was added 1M tetrabutylammonium fluoride in THF (0.63 mL, 0.63 mmol). The reaction was stirred at room temperature for 1 h and was then diluted with ethyl acetate, poured into 1N HCl, and extracted twice with ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate, filtered, and concentrated. The residue was purified by flash chromatography eluting with 5% methanol in methylene chloride to afford the title compound (125 mg).

Workup

  1. extractionextracted twice with ethyl acetate
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography
  7. washeluting with 5% methanol in methylene chloride

Sources & evidence

ORD record
ord-22577971d76249afb71b0146d403c604
Source dataset
uspto-grants-2006_08
Patent number
US07091211B2

Reaction notes

Loading…