Bromoacetic Acid → 2-(5-Methoxy-1-oxo-1,3-dihydrospiro[indene-2,4'-piperidine]-1'-yl)acetic acid

HRID 713405Notes

Reaction equation

HRID 713405 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:14](=[CH:15][CH:16]=1)[C:13](=[O:17])[C:7]1([CH2:12][CH2:11][NH:10][CH2:9][CH2:8]1)[CH2:6]2.Br[CH2:19][C:20]([OH:22])=[O:21].CCN(C(C)C)C(C)C>CN(C=O)C.C(OCC)(=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:14](=[CH:15][CH:16]=1)[C:13](=[O:17])[C:7]1([CH2:12][CH2:11][N:10]([CH2:19][C:20]([OH:22])=[O:21])[CH2:9][CH2:8]1)[CH2:6]2

Participants

6

Reactant 3

HCID 6227Bromoacetic AcidHCID 81531DiisopropylethylamineHCID 71212150HCID 71212150, compound

Product 1

HCID 712360552-(5-Methoxy-1-oxo-1,3-dihydrospiro[indene-2,4'-piperidine]-1'-yl)acetic acidYield 65.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A stirred solution of 5-methoxyspiro[indene-2,4′-piperidin]-1(3H)-one (511 mg, 1.93 mmol), bromoacetic acid (349 mg, 2.51 mmol) and DIPEA (1.013 mL, 5.80 mmol) in DMF (5 mL) was heated at 100° C. for 20 min via microwave. The reaction mixture was diluted with 20 mL of ethyl acetate, washed with 5 mL of water, dried over Na2SO4 and concentrated in vacuo. The crude product was purified by flash column (gradient of 100:0 to 85:15 CH2Cl2/MeOH with 5% NH4OH over 20 min) to give the title compound (368 mg, 1.272 mmol). MS calculated for C16H19NO4 290.3. found (ESI) m/z 290.1 (M+H)+, retention time 1.10 min.

Workup

  1. washwashed with 5 mL of water
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. customThe crude product was purified by flash column (gradient of 100:0 to 85:15 CH2Cl2/MeOH with 5% NH4OH over 20 min)

Sources & evidence

ORD record
ord-1e062f68d0e040929dc0ffaed3e098d2
Source dataset
uspto-grants-2015_11
Patent number
US09181266B2

Reaction notes

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