Sodium Bicarbonate → 1'-(tert-Butoxycarbonyl)-4-oxo-3,4-dihydrospiro[1-benzopyran-2,4'-piperidine]-6-carboxylic acid

HRID 545213Notes

Reaction equation

HRID 545213 reaction equation
Cl.[C:2]([C:5]1[CH:6]=[C:7]2[C:17](=[CH:18][CH:19]=1)[O:16][C:10]1([CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1)[CH2:9][C:8]2=[O:20])([OH:4])=[O:3].[C:21]([O-:24])(O)=[O:22].[Na+]>O1CCOCC1.O.CCOCC.[OH-].[Na+]>[C:2]([C:5]1[CH:6]=[C:7]2[C:17](=[CH:18][CH:19]=1)[O:16][C:10]1([CH2:11][CH2:12][N:13]([C:21]([O:24][C:5]([CH3:6])([CH3:19])[CH3:2])=[O:22])[CH2:14][CH2:15]1)[CH2:9][C:8]2=[O:20])([OH:4])=[O:3]

Participants

7

Reactant 2

HCID 516892Sodium BicarbonateHCID 66782663HCID 66782663, compound

Product 1

HCID 509991921'-(tert-Butoxycarbonyl)-4-oxo-3,4-dihydrospiro[1-benzopyran-2,4'-piperidine]-6-carboxylic acid

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 14798Sodium HydroxideSolventHCID 312751,4-DioxaneSolvent

Procedure

6-Carboxy-4-oxospiro(chroman-2,4′-piperidine) hydrochloride (15.0 g, 50.3 mmol) was dissolved in 1,4-dioxane (150 ml) and H2O (150 ml), NaHCO3 (10.6 g, 126 mmol) and DIBOC (13.2 g, 60.4 mmol) were added thereto in this order. After stirred at room temperature for 13 h, the reaction mixture was diluted with Et2O and 5N NaOH aq. (12.1 ml). The aqueous layer was washed with Et2O and acidified with 6N HCl aq. (PH=ca. 3), then extracted with CHCl3. The organic layer was washed with brine and dried over MgSO4. The desiccant was removed through filtration and the filtrate was concentrated under reduced pressure. The residue was triturated with MeOH—H2O and the insoluble solid was collected through filtration to obtain the intended compound as a colorless solid.

Workup

  1. washThe aqueous layer was washed with Et2O
  2. extractionextracted with CHCl3
  3. washThe organic layer was washed with brine
  4. dry with materialdried over MgSO4
  5. customThe desiccant was removed through filtration
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customThe residue was triturated with MeOH—H2O
  8. filtrationthe insoluble solid was collected through filtration

Sources & evidence

ORD record
ord-e5924a9af78a436e9611a942597a3692
Source dataset
uspto-grants-2011_05
Patent number
US07935712B2

Reaction notes

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