Ethyl bromoacetate → HCID 71227315, compound

HRID 713407Notes

Reaction equation

HRID 713407 reaction equation
[NH:1]1[CH2:6][CH2:5][C:4]2([CH2:15][CH2:14][C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7]2=[O:16])[CH2:3][CH2:2]1.Br[CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20].C(N(CC)CC)C>C(#N)C.C(OCC)(=O)C>[O:16]=[C:7]1[C:4]2([CH2:3][CH2:2][N:1]([CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH2:6][CH2:5]2)[CH2:15][CH2:14][C:13]2[C:8]1=[CH:9][CH:10]=[CH:11][CH:12]=2

Participants

6

Reactant 3

HCID 7748Ethyl bromoacetateHCID 8471TriethylamineHCID 9794387HCID 9794387, compound

Product 1

HCID 71227315HCID 71227315, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
25 °C

Procedure

A solution of 3,4-dihydro-1H-spiro[naphthalene-2,4′-piperidin]-1-one (72 mg, 0.286 mmol), ethyl bromoacetate (62.1 mg, 0.37 mmol) and triethylamine (0.20 mL, 1.43 mmol) in acetonitrile (5 ml) was heated at 80° C. for 3 h. The reaction was cooled to 25° C. and diluted with 20 mL of ethyl acetate and washed twice with 10 mL of water, dried over Na2SO4 and concentrated. The crude product was purified by flash chromatography (gradient of 85:15 to 60:40 heptane/ethyl acetate over 20 min) to give the title compound as a white solid. MS calculated for C18H24NO3 302.4. found (ESI) m/z 302.5 (M+H)+, retention time 0.81 min.

Workup

  1. washwashed twice with 10 mL of water
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated
  4. customThe crude product was purified by flash chromatography (gradient of 85:15 to 60:40 heptane/ethyl acetate over 20 min)

Sources & evidence

ORD record
ord-33ae5cfe551e425eacbec7727e531032
Source dataset
uspto-grants-2015_11
Patent number
US09181266B2

Reaction notes

Loading…