Boron trifluoride etherate → HCID 58015015, compound

HRID 1676516Notes

Reaction equation

HRID 1676516 reaction equation
N1([CH2:10][NH:11][CH:12]2[CH2:16][CH2:15][CH2:14][CH2:13]2)C2C=CC=CC=2N=N1.[Cl:17][C:18]([Cl:27])=[C:19]([O:25][CH3:26])[O:20][Si](C)(C)C.B(F)(F)F.CCOCC>ClCCl>[CH3:26][O:25][C:19](=[O:20])[C:18]([Cl:27])([Cl:17])[CH2:10][NH:11][CH:12]1[CH2:13][CH2:14][CH2:15][CH2:16]1

Participants

5

Reactant 3

HCID 8000Boron trifluoride etherateHCID 5235843N-(benzotriazol-1-ylmethyl)cyclopentanamineHCID 11435856(2,2-Dichloro-1-methoxy-vinyloxy)-trimethylsilane

Product 1

HCID 58015015HCID 58015015, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4.3 g (0.02 mole) of benzotriazol-1-ylmethyl-cyclopentyl-amine and 6.4 g (0.030 mole) of (2,2-dichloro-1-methoxy-vinyloxy)-trimethyl-silane in 140 ml of anhydrous dichloromethane was added dropwise 3.7 ml (0.030 mole) of boron trifluride diethyl etherate at 0 degrees. The reaction was stirred at 0 degrees for 1 hour and then at room temperature for 24 hours. The reaction was quenched by the addition of 10% aqueous sodium carbonate and extracted with dichloromethane. The organic layer was washed with saturated sodium carbonate, brine, dried over sodium sulfate, filtered and concentrated under reduced pressure. Purification by silica gel chromatography, eluting with hexane-ethyl acetate (gradient, 100:0-85:15) gave 2.4 g of 2,2-dichloro-3-cyclopentylamino-propionic acid methyl ester as a colorless oil.

Workup

  1. waitat room temperature for 24 hours
  2. customThe reaction was quenched by the addition of 10% aqueous sodium carbonate
  3. extractionextracted with dichloromethane
  4. washThe organic layer was washed with saturated sodium carbonate, brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customPurification by silica gel chromatography
  9. washeluting with hexane-ethyl acetate (gradient, 100:0-85:15)

Sources & evidence

ORD record
ord-e20c866e1bea4a4ea87b82551f32de27
Source dataset
uspto-grants-2011_08
Patent number
US08003785B2

Reaction notes

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