Dimethylformamide → methyl (S)-2-benzylamino-3-cycloheptyl-propionate

HRID 1615737Notes

Reaction equation

HRID 1615737 reaction equation
[NH2:1][C@@H:2]([CH2:7][CH:8]1[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1)[C:3]([O:5][CH3:6])=[O:4].[CH2:15](Br)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(=O)([O-])[O-].[K+].[K+].CN(C=O)C>O>[CH2:15]([NH:1][C@@H:2]([CH2:7][CH:8]1[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1)[C:3]([O:5][CH3:6])=[O:4])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 68795663Methyl (S)-2-amino-3-cycloheptylpropanoate

Product 1

HCID 68790091methyl (S)-2-benzylamino-3-cycloheptyl-propionate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1.04 g (5.22 mmol) methyl (S)-2-amino-3-cycloheptyl-propionate were stirred with 0.62 ml (5.22 mmol) benzylbromide, 1.44 g (10.4 mmol) potassium carbonate and 20 ml DMF at 100° C. for 3.5 h. Then water was added and the mixture was extracted with ethyl acetate. The organic phase was evaporated down and the residue was purified by flash chromatography.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. customThe organic phase was evaporated down
  3. customthe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-a9a63f0c461241f7a8b0287ae3d987f5
Source dataset
uspto-grants-2014_07
Patent number
US08765763B2

Reaction notes

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