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Benzyl Bromide → methyl 2(S)-(N,N-dibenzylamino)-3-cyclohexylpropionate

HRID 259830
Notes
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Reaction equation

HRID 259830 reaction equation
Cl.[NH2:2][C@@H:3]([CH2:8][CH:9]1[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1)[C:4]([O:6][CH3:7])=[O:5].C(=O)([O-])[O-].[K+].[K+].[CH2:21](Br)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>CN(C)C=O>[CH2:21]([N:2]([C@@H:3]([CH2:8][CH:9]1[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1)[C:4]([O:6][CH3:7])=[O:5])[CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 22861687methyl (2S)-2-amino-3-cyclohexylpropanoate hydrochloride

Product 1

HCID 22861690methyl 2(S)-(N,N-dibenzylamino)-3-cyclohexylpropionateYield 165.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

Methyl 2(S)-amino-3-cyclohexylpropionate hydrochloride (150 g) was dissolved in N,N-dimethylformamide (1200 ml). Thereto was added pulverized potassium carbonate (330.7 g), and benzyl bromide (254.6 g) was dropwise added to the obtained suspension while stirring. After the dropwise addition, the inner temperature was raised to 50° C., and the reaction mixture was stirred at said temperature for 9 hours. The reaction mixture was cooled and filtered. Water (600 ml) and diisopropyl ether (600 ml) were added to the filtrate for partition, and the organic layer was separated. The water layer was re-extracted with diisopropyl ether (300 ml), and the combined organic layer was washed with 5% hydrochloric acid (600 ml), 5% aqueous sodium hydrogencarbonate (600 ml), and 25% aqueous sodium chloride sequentially and dried over magnesium sulfate. The solvent was distilled away to give 204.6 g of methyl 2(S)-(N,N-dibenzylamino)-3-cyclohexylpropionate.

Workup

  1. additionThereto was added
  2. additionwas dropwise added to the obtained suspension
  3. additionAfter the dropwise addition
  4. stirringthe reaction mixture was stirred
  5. customfor 9 hours
  6. temperatureThe reaction mixture was cooled
  7. filtrationfiltered
  8. additionWater (600 ml) and diisopropyl ether (600 ml) were added to the filtrate
  9. customfor partition
  10. customthe organic layer was separated
  11. extractionThe water layer was re-extracted with diisopropyl ether (300 ml)
  12. washthe combined organic layer was washed with 5% hydrochloric acid (600 ml), 5% aqueous sodium hydrogencarbonate (600 ml), and 25% aqueous sodium chloride sequentially
  13. dry with materialdried over magnesium sulfate
  14. distillationThe solvent was distilled away

Sources & evidence

ORD record
ord-85783abc216c48f4ba83c5bfc44774a9
Source dataset
uspto-grants-1996_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05523410

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes