Pyridine → 2-Oxo-2-[(1-oxo-2,3-dihydro-1H-inden-5-yl)amino]ethyl acetate

HRID 1690697Notes

Reaction equation

[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[CH2:6][CH2:5]2.N1C=CC=CC=1.[C:18]([O:21][CH2:22][C:23](Cl)=[O:24])(=[O:20])[CH3:19]>C(Cl)Cl>[O:11]=[C:7]1[C:8]2[C:4](=[CH:3][C:2]([NH:1][C:23]([CH2:22][O:21][C:18](=[O:20])[CH3:19])=[O:24])=[CH:10][CH:9]=2)[CH2:5][CH2:6]1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 5-Amino-indan-1-one (commercially available, 100 mg, 0.679 mmol, 1 eq.) in DCM (5 mL) is added pyridine (0.066 mL, 0.815 mmol, 1.2 eq.). The resulting solution is cooled to 0° C. followed by the addition of acetoxy acetyl chloride (0.073 mL, 0.679 mmol, 1 eq.). After stirring at 0° C. for 15 min., the reaction is warmed to 25° C. and stirred for 12 h. The reaction is diluted with DCM and sequentially washed with 1 N HCl (aq) and saturated aqueous NaHCO3. The resulting organic solution is dried over Na2SO4. After concentration, the residue is purified by silica gel chromatography (1:6 hexanes/EtOAc) to give Acetic acid (1-oxo-indan-5-ylcarbamoyl)-methyl ester as an off-white solid (136 mg, 81% yield). [MS: (ES+) 248.1 (M+1)+].

Workup

temperaturethe reaction is warmed to 25° C.
stirringstirred for 12 h
washsequentially washed with 1 N HCl (aq) and saturated aqueous NaHCO3
dry with materialThe resulting organic solution is dried over Na2SO4
concentrationAfter concentration
customthe residue is purified by silica gel chromatography (1:6 hexanes/EtOAc)

Sources & evidence

ORD record: ord-52b4d875745d4977b63af33ccdd9f43d
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08153671B2

Reaction notes

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