Sodium Bicarbonate → HCID 59714871, compound

HRID 2223938Notes

Reaction equation

HRID 2223938 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([CH2:34][CH2:35][N:36]2[CH2:41][CH2:40][CH:39]([N:42]([C:50]3[CH:55]=[CH:54][C:53]([CH3:56])=[CH:52][CH:51]=3)[C:43]([C:45]3[O:46][CH:47]=[CH:48][CH:49]=3)=[O:44])[CH2:38][CH2:37]2)([CH2:14][CH2:15][O:16][Si](C(C)(C)C)(C2C=CC=CC=2)C2C=CC=CC=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O1CCCC1.C(=O)(O)[O-].[Na+]>O1CCCC1>[CH2:1]([N:8]1[CH2:9][CH2:10][C:11]([CH2:34][CH2:35][N:36]2[CH2:37][CH2:38][CH:39]([N:42]([C:50]3[CH:55]=[CH:54][C:53]([CH3:56])=[CH:52][CH:51]=3)[C:43]([C:45]3[O:46][CH:47]=[CH:48][CH:49]=3)=[O:44])[CH2:40][CH2:41]2)([CH2:14][CH2:15][OH:16])[CH2:12][CH2:13]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 11078149TBAF tetrahydrofuranHCID 59714968HCID 59714968, compound

Product 1

HCID 59714871HCID 59714871, compoundYield 63.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-[1-[2-[1-benzyl-4-[2-(tert-butyldiphenylsiloxy)ethyl]piperidin-4-yl]ethyl]piperidin-4-yl]-N-(p-tolyl)-2-furancarboxamide (synthesized in Example 87) (0.73 g) in tetrahydrofuran (3 mL) was added 1M tetra n-butylammonium fluoride/tetrahydrofuran (1.9 mL). The reaction solution was stirred at room temperature for 15 hours. Saturated aqueous sodium bicarbonate solution was added to the solution and it was extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting residue was purified by chromatography [NH silica gel, chloroform-methanol (98:2) ] to give the title compound (0.32 g.)

Workup

  1. extractionwas extracted with ethyl acetate
  2. washThe organic layer was washed with saturated aqueous sodium chloride solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by chromatography [NH silica gel, chloroform-methanol (98:2) ]

Sources & evidence

ORD record
ord-6abb6510e2c142d1bc509299d95d12f8
Source dataset
uspto-grants-2008_05
Patent number
US07375115B2

Reaction notes

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