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

HRID 713402Notes

Reaction equation

HRID 713402 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:13](=[CH:14][CH:15]=1)[C:12](=[O:16])[C:6]1([CH2:11][CH2:10][NH:9][CH2:8][CH2:7]1)[CH2:5]2.Br[CH2:18][C:19]([OH:21])=[O:20].C(N(CC)CC)C>C(#N)C.C(OCC)(=O)C>[F:1][C:2]1[CH:3]=[C:4]2[C:13](=[CH:14][CH:15]=1)[C:12](=[O:16])[C:6]1([CH2:11][CH2:10][N:9]([CH2:18][C:19]([OH:21])=[O:20])[CH2:8][CH2:7]1)[CH2:5]2

Participants

6

Reactant 3

HCID 6227Bromoacetic AcidHCID 8471TriethylamineHCID 712121695-Fluorospiro[indene-2,4'-piperidin]-1(3H)-one

Product 1

HCID 712360652-(5-Fluoro-1-oxo-1,3-dihydrospiro[indene-2,4'-piperidine]-1'-yl)acetic acidYield 100%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
25 °C

Procedure

A stirred solution of 5-fluorospiro[indene-2,4′-piperidin]-1(3H)-one (160 mg, 0.626 mmol), bromoacetic acid (113 mg, 0.813 mmol) and triethylamine (0.436 mL, 3.13 mmol) in acetonitrile (2 mL) was heated at 80° C. for 3 h, then cooled to 25° C. The reaction mixture was diluted with 20 mL of ethyl acetate and washed with 5 mL of water, dried over Na2SO4 and concentrated to dryness without any further purification to give the title compound (174 mg, 0.626 mmol, 100% yield). MS calculated for C15H17FNO3 278.3. found (ESI) m/z 278.4 (M+H)+, retention time 0.81 min.

Workup

  1. washwashed with 5 mL of water
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated to dryness without any further purification

Sources & evidence

ORD record
ord-f9800230e8614f25844c8290756ae6af
Source dataset
uspto-grants-2015_11
Patent number
US09181266B2

Reaction notes

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