Allyl bromide → N-{[(7S)-3,4-Dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl]-methyl}prop-2-en-1-amine

HRID 657543Notes

Reaction equation

HRID 657543 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:8](=[CH:9][C:10]=1[O:11][CH3:12])[C@@H:7]([CH2:13][NH2:14])[CH2:6]2.C(=O)([O-])[O-].[K+].[K+].[CH2:21](Br)[CH:22]=[CH2:23]>CC(C)=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:8](=[CH:9][C:10]=1[O:11][CH3:12])[C@@H:7]([CH2:13][NH:14][CH2:23][CH:22]=[CH2:21])[CH2:6]2

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 115066164,5-Dimethoxy-1-(aminomethyl)benzocyclobutane, (S)-

Product 1

HCID 68973512N-{[(7S)-3,4-Dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl]-methyl}prop-2-en-1-amine

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To 3.9 g (20 mmol) of {[(7S)-3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl]methyl}amine in 40 mL of acetone, at ambient temperature, there are added, all at once, 4.1 g (30 mmol/1.5 eq.) of potassium carbonate, and then there are quickly added dropwise 1.9 mL (22 mmol/1.1 eq.) of allyl bromide. Stirring is carried out at ambient temperature for 60 hours; the salts are then filtered off and the filtrate is concentrated. The residue (4.8 g) is chromatographed over 300 g of silica (eluant: dichloromethane/ethanol/ammonia: 98/2/0.2) to yield the desired product.

Workup

  1. filtrationthe salts are then filtered off
  2. concentrationthe filtrate is concentrated
  3. customThe residue (4.8 g) is chromatographed over 300 g of silica (eluant: dichloromethane/ethanol/ammonia: 98/2/0.2)

Sources & evidence

ORD record
ord-7f9a7dbae62044239062f571b7ec6ddc
Source dataset
uspto-grants-2011_12
Patent number
US08076325B2

Reaction notes

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