Methyl chloroformate → HCID 57618505, compound

HRID 1690698Notes

Reaction equation

HRID 1690698 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.C[CH2:13][O:14][C:15](C)=[O:16].O.C([O-])(O)=O.[Na+].ClC(OC)=O>CCOC(C)=O>[CH3:13][O:14][C:15](=[O:16])[NH: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

Participants

6

Reactant 4

HCID 6586Methyl chloroformateHCID 3128905-amino-2,3-dihydro-1H-inden-1-oneHCID 516892Sodium BicarbonateHCID 22728543Water ethylacetate

Product 1

HCID 57618505HCID 57618505, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a suspension of 5-Amino-indan-1-one (commercially available, 100 mg, 0.679 mmol, 1 eq.) in a 2:1 v/v mixture of EtOAc/H2O (6 mL) is added NaHCO3 (114 mg, 1.36 mmol, 2 eq.). The resulting mixture is cooled to 0° C. followed by the addition of methyl chloroformate (0.052 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 EtOAc and sequentially washed with 1 N HCl (aq) and saturated aqueous NaCl. The resulting organic solution is dried over Na2SO4 and concentrated to give (1-Oxo-indan-5-yl)-carbamic acid methyl ester as a tan solid (124 mg, 89% yield). [MS: (ES+) 206.1 (M+1)+].

Workup

  1. temperaturethe reaction is warmed to 25° C.
  2. stirringstirred for 12 h
  3. washsequentially washed with 1 N HCl (aq) and saturated aqueous NaCl
  4. dry with materialThe resulting organic solution is dried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-72df77091fe04ba086879b535f644a4d
Source dataset
uspto-grants-2012_04
Patent number
US08153671B2

Reaction notes

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