Potassium Carbonate → Ethyl 3-[2-fluoro-4-[[4-(spiro[indane-1,4'-piperidine]-1'-ylmethyl)phenyl]methoxy]phenyl]propanoate

HRID 390401Notes

Reaction equation

HRID 390401 reaction equation
Br[CH2:2][C:3]1[CH:23]=[CH:22][C:6]([CH2:7][N:8]2[CH2:13][CH2:12][C:11]3([C:21]4[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=4)[CH2:15][CH2:14]3)[CH2:10][CH2:9]2)=[CH:5][CH:4]=1.[F:24][C:25]1[CH:30]=[C:29]([OH:31])[CH:28]=[CH:27][C:26]=1[CH2:32][CH2:33][C:34]([O:36][CH2:37][CH3:38])=[O:35].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.O>[F:24][C:25]1[CH:30]=[C:29]([O:31][CH2:2][C:3]2[CH:23]=[CH:22][C:6]([CH2:7][N:8]3[CH2:13][CH2:12][C:11]4([C:21]5[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=5)[CH2:15][CH2:14]4)[CH2:10][CH2:9]3)=[CH:5][CH:4]=2)[CH:28]=[CH:27][C:26]=1[CH2:32][CH2:33][C:34]([O:36][CH2:37][CH3:38])=[O:35]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 23082888Ethyl 3-(2-fluoro-4-hydroxyphenyl)propanoateHCID 670872261'-[4-(Bromomethyl)benzyl]-2,3-dihydrospiro[indene-1,4'-piperidine]

Product 1

HCID 67086942Ethyl 3-[2-fluoro-4-[[4-(spiro[indane-1,4'-piperidine]-1'-ylmethyl)phenyl]methoxy]phenyl]propanoateYield 46.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 1′-[4-(bromomethyl)benzyl]-2,3-dihydrospiro[indene-1,4′-piperidine] (0.35 g, 0.94 mmol), ethyl 3-(2-fluoro-4-hydroxyphenyl)propanoate (0.2 g, 0.94 mmol) and K2CO3 (0.32 g, 2.3 mmol) in DMF (15 mL) is stirred overnight at room temperature. The reaction mixture is diluted with cold water and extracted with DCM (3×50 mL). The combined organic layer is washed with brine solution, dried over Na2SO4, and concentrated under vacuum. The crude material is purified by silica gel chromatography (gradient DCM/MeOH 8/2) to give the title compound as an off-white solid (0.22 g, crude). ESI/MS 502 (M+H)+.

Workup

  1. extractionextracted with DCM (3×50 mL)
  2. washThe combined organic layer is washed with brine solution
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under vacuum
  5. customThe crude material is purified by silica gel chromatography (gradient DCM/MeOH 8/2)

Sources & evidence

ORD record
ord-23f34165d791452689ed16be686e9305
Source dataset
uspto-grants-2013_02
Patent number
US08383642B2

Reaction notes

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