Potassium Carbonate → HCID 68175904, compound

HRID 408584Notes

Reaction equation

HRID 408584 reaction equation
C([O-])([O-])=O.[K+].[K+].[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([C@H:14]([NH2:16])[CH3:15])=[CH:10][CH:9]=1.[CH3:17][O:18][C:19](=[O:24])[CH2:20][CH2:21][CH2:22]Br>CC#N>[CH3:17][O:18][C:19](=[O:24])[CH2:20][CH2:21][CH2:22][NH:16][C@@H:14]([C:11]1[CH:12]=[CH:13][C:8]([Cl:7])=[CH:9][CH:10]=1)[CH3:15]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 107604Methyl 4-bromobutyrateHCID 1715226(1R)-1-(4-chlorophenyl)ethan-1-amine

Product 1

HCID 68175904HCID 68175904, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
20 °C

Procedure

To a suspension of K2CO3 (1.5 eq.) and (R)-1-(4-chloro-phenyl)-ethylamine (0.9 eq.) in MeCN was added 4-bromo-butyric acid methyl ester (1 eq.) and KI (0.1 eq.). The reaction was stirred for 15 h at 20° C., then heated to reflux until completion. The crude was partitioned between water and EtOAc. The organic layer was washed with brine, dried over MgSO4, filtered and concentrated under reduced pressure. The crude was purified by chromatography on silica gel (elution with DCM/MeOH: 99/1 to 90/10) to afford 4-[(R)-1-(4-chloro-phenyl)-ethylamino]-butyric acid methyl ester.

Workup

  1. temperatureheated
  2. temperatureto reflux until completion
  3. customThe crude was partitioned between water and EtOAc
  4. washThe organic layer was washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe crude was purified by chromatography on silica gel (elution with DCM/MeOH: 99/1 to 90/10)

Sources & evidence

ORD record
ord-b62436cb766f463581c4388e2d149e6a
Source dataset
uspto-grants-2014_06
Patent number
US08759334B2

Reaction notes

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