Potassium Carbonate → tert-butyl 2-[(2,3-dihydro-1H-inden-2-yl)amino]acetate

HRID 1456660Notes

Reaction equation

HRID 1456660 reaction equation
Cl.[NH2:2][CH:3]1[CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4]1.C([O-])([O-])=O.[K+].[K+].Br[CH2:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21]>CCO.CCOC(C)=O>[C:23]([O:22][C:20](=[O:21])[CH2:19][NH:2][CH:3]1[CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4]1)([CH3:26])([CH3:25])[CH3:24]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 79177tert-Butyl bromoacetateHCID 1227642-Aminoindan hydrochloride

Product 1

HCID 13132278tert-butyl 2-[(2,3-dihydro-1H-inden-2-yl)amino]acetateYield 64.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of 2-aminoindane hydrochloride (5.0g, 29.5 mmol) and powdered K2CO3 (8.3 g, 60.0 mmol) in absolute EtOH (30 mL) was added tert-butyl bromoacetate (4.4 mL, 29.5 mmol). After stirring for 10 min at rt the reaction was heated to 45° C. and stirred for 2 hr. The reaction was cooled to rt, diluted with EtOAc, filtered and concentrated. Chromatography of the residue on silica gel (elution with 20% EtOAc:hexane) provided 4.7g of compound 721 as a white crystalline solid. ##STR100##

Workup

  1. temperaturewas heated to 45° C.
  2. stirringstirred for 2 hr
  3. temperatureThe reaction was cooled to rt
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-015dabe5ec2c4dbb9a812f252e009f8b
Source dataset
uspto-grants-1998_12
Patent number
US05843904

Reaction notes

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