Sodium Bicarbonate → HCID 9930379, compound

HRID 2084602Notes

Reaction equation

HRID 2084602 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([C:14](=[O:34])[C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([O:21][Si:22]([CH:29]([CH3:31])[CH3:30])([CH:26]([CH3:28])[CH3:27])[CH:23]([CH3:25])[CH3:24])[C:16]=2[O:32][CH3:33])[CH2:10][CH2:9]1)=O)(C)(C)C.C([O-])(O)=O.[Na+]>FC(F)(F)C(O)=O>[CH3:33][O:32][C:16]1[C:17]([O:21][Si:22]([CH:23]([CH3:25])[CH3:24])([CH:29]([CH3:31])[CH3:30])[CH:26]([CH3:28])[CH3:27])=[CH:18][CH:19]=[CH:20][C:15]=1[C:14]([CH:11]1[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]1)=[O:34]

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 9805653HCID 9805653, compound

Product 1

HCID 9930379HCID 9930379, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

Stir and cool in an ice bath under nitrogen, 4-(2-methoxy-3-triisopropylsilanyloxy-benzoyl)-piperidine-1-carboxylic acid tert-butyl ester, Example 2B (5.71 g, 11.6 mmol) and add trifluoroacetic acid (30 mL). Remove the cold bath after 10 minutes. After 2 h, concentrate the reaction under vacuum at 40-45° C. and then pour into saturated aqueous NaHCO3. Extract the basic layer with CH2Cl2 (2×200 mL), dry (Na2SO4), and concentrate under vacuum to an oil, which eventually solidifies to afford 4-(2-methoxy-3-triisopropylsilanyloxy-benzoyl)-piperidine.

Workup

  1. temperaturecool in an ice bath under nitrogen
  2. customRemove the cold bath after 10 minutes
  3. concentrationconcentrate
  4. customthe reaction under vacuum at 40-45° C.
  5. extractionExtract the basic layer with CH2Cl2 (2×200 mL)
  6. dry with materialdry (Na2SO4)
  7. concentrationconcentrate under vacuum to an oil, which

Sources & evidence

ORD record
ord-f561513b6e5f4d6196137f91284ad18e
Source dataset
uspto-grants-2004_04
Patent number
US06716986B2

Reaction notes

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