2,4-Dimethoxybenzylamine → HCID 18639903, compound

HRID 2108184Notes

Reaction equation

HRID 2108184 reaction equation
[CH:1]([C@@H:3]1[C@H:5]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)[O:4]1)=O.[CH3:12][O:13][C:14]1[CH:21]=[C:20]([O:22][CH3:23])[CH:19]=[CH:18][C:15]=1[CH2:16][NH2:17]>ClCCl>[CH3:12][O:13][C:14]1[CH:21]=[C:20]([O:22][CH3:23])[CH:19]=[CH:18][C:15]=1[CH2:16][N:17]=[CH:1][C@H:3]1[C@H:5]([C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=2)[O:4]1

Participants

4

Reactant 2

HCID 5972502,4-DimethoxybenzylamineHCID 57031949HCID 57031949, compound

Product 1

HCID 18639903HCID 18639903, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of (2S,3S)-2-formyl-3-phenyloxirane (430 mg, 2.90 mmol) in 8.0 mL of dichloromethane under nitrogen was added a solution of 2,4-dimethoxybenzylamine (461 mg, 2.75 mmol) in 1.0 mL of dichloromethane via cannula. Residual amine was washed into the reaction flask with 1.0 mL of dichloromethane. Molecular sieves (2.3 g of pellets, 4 Å, activated) were added and the mixture was allowed to stand for 12 hours. This solution was used directly in the cycloaddition after removing and concentrating a small aliquot for spectral analysis: IR (CHCl3) 3016, 1615, 1510 cm-1 ; 1H NMR (CDCl3, 250 MHz) δ 7.40-7.24 (6H, N=CH, ArH), 7.14 (d, 1H, J=8.8 Hz, ArH), 6.52-6.43 (2H, ArH), 4.62 (s, 2H, NCH2Ar), 3.69 (d, 1H, J=1.9 Hz, oxirane CHCHPh), 3.82 (s, 3H, OCH3), 3.81 (s, 3H, OCH3), 3.62 (dd, 1H, J=1.9, 7.0 Hz, oxirane CHCHPh).

Workup

  1. washResidual amine was washed into the reaction flask with 1.0 mL of dichloromethane
  2. additionMolecular sieves (2.3 g of pellets, 4 Å, activated) were added
  3. customafter removing
  4. concentrationconcentrating a small aliquot for spectral analysis

Sources & evidence

ORD record
ord-8be00347fb34439f80f16f0dcabb5b46
Source dataset
uspto-grants-1990_06
Patent number
US04937331

Reaction notes

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