Triethylamine → HCID 66927008, compound

HRID 1022933Notes

Reaction equation

HRID 1022933 reaction equation
[C:1]1([CH2:7][NH:8][CH2:9][C@H:10]2[CH2:14][CH2:13][CH2:12][NH:11]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.Br[CH:23]([CH2:28]Br)[C:24]([O:26][CH3:27])=[O:25]>C1(C)C=CC=CC=1.C(OCC)C.[Cl-].[Na+].O>[CH2:7]([N:8]1[C@H:23]([C:24]([O:26][CH3:27])=[O:25])[CH2:28][N:11]2[CH2:12][CH2:13][CH2:14][C@@H:10]2[CH2:9]1)[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 95428Methyl 2,3-dibromopropionateHCID 8027396HCID 8027396, compound

Product 1

HCID 66927008HCID 66927008, compoundYield 45.9%

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 3283Diethyl EtherSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
90 °C

Procedure

To a suspension of 1-phenyl-N-[(2R)-pyrrolidin-2-ylmethyl]methanamine (13.6 g) in toluene (120 mL) were added triethylamine (22.9 mL) and methyl 2,3-dibromopropanoate (13.4 g) under ice-cooling, and the mixture was stirred with heating at 90° C. for 5 hr. The reaction mixture was allowed to cool to room temperature, and diluted with diethyl ether (200 mL) and brine (200 mL). The organic layer was dried over anhydrous magnesium sulfate, and the insoluble material was filtered off. The filtrate was concentrated under reduced pressure, and purified by silica gel column chromatography (ethyl acetate/hexane=10/80→50/50) to give the title compound (6.86 g) as a pale-yellow oil.

Workup

  1. temperaturecooling
  2. temperatureto cool to room temperature
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. filtrationthe insoluble material was filtered off
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. custompurified by silica gel column chromatography (ethyl acetate/hexane=10/80→50/50)

Sources & evidence

ORD record
ord-b3ecb36de6b84a9386ac4c1f573e283f
Source dataset
uspto-grants-2014_05
Patent number
US08722660B2

Reaction notes

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