Triethylamine → [2-(tert-Butyldimethylsilanyloxymethyl)allyl]-(2,4-dimethoxybenzyl)amine

HRID 83572Notes

Reaction equation

HRID 83572 reaction equation
[Si:1]([O:8][CH2:9][C:10](=[CH2:13])[CH2:11]O)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C(N(CC)CC)C.CS(Cl)(=O)=O.[CH3:26][O:27][C:28]1[CH:35]=[C:34]([O:36][CH3:37])[CH:33]=[CH:32][C:29]=1[CH2:30][NH2:31]>C(Cl)(Cl)Cl.O>[Si:1]([O:8][CH2:9][C:10](=[CH2:13])[CH2:11][NH:31][CH2:30][C:29]1[CH:32]=[CH:33][C:34]([O:36][CH3:37])=[CH:35][C:28]=1[O:27][CH3:26])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 8471Triethylamine2×HCID 31297Methanesulfonyl chlorideHCID 5972502,4-DimethoxybenzylamineHCID 112064702-(((Tert-butyldimethylsilyl)oxy)methyl)prop-2-en-1-ol

Product 1

HCID 89465872[2-(tert-Butyldimethylsilanyloxymethyl)allyl]-(2,4-dimethoxybenzyl)amine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

To a solution of 2-(tert-butyldimethylsilanyloxymethyl)-2-propen-1-ol (1.58 g) in chloroform (16 ml) were sequentially added triethylamine (2.2 ml) and methanesulfonyl chloride (0.73 ml) at 0° C., and then the mixture was stirred for 2 hours. To this reaction solution were sequentially added triethylamine (1.2 ml) and 2,4-dimethoxybenzylamine (1.3 ml), and then the mixture was stirred at room temperature for 15 hours. To this reaction mixture was added water, and an organic layer was separated from the mixture, and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=1/1) to give the titled compound (1.14 g).

Workup

  1. customat 0° C.
  2. stirringthe mixture was stirred at room temperature for 15 hours
  3. customan organic layer was separated from the mixture
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-fd2cef5176184b4e8118db8754e71253
Source dataset
uspto-grants-2014_09
Patent number
US08846746B2

Reaction notes

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