Triethylsilane → Ethyl 3-[3-(aminomethyl)-4-methoxyphenyl]-2-isopropoxypropanoate

HRID 1985294Notes

Reaction equation

HRID 1985294 reaction equation
C(OC([NH:8][CH2:9][C:10]1[CH:11]=[C:12]([CH:18](O)[CH:19]([O:25][CH:26]([CH3:28])[CH3:27])[C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH:13]=[CH:14][C:15]=1[O:16][CH3:17])=O)(C)(C)C.C([SiH](CC)CC)C>FC(F)(F)C(O)=O>[NH2:8][CH2:9][C:10]1[CH:11]=[C:12]([CH2:18][CH:19]([O:25][CH:26]([CH3:27])[CH3:28])[C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH:13]=[CH:14][C:15]=1[O:16][CH3:17]

Participants

4

Reactant 2

HCID 12052TriethylsilaneHCID 22494370HCID 22494370, compound

Product 1

HCID 22493983Ethyl 3-[3-(aminomethyl)-4-methoxyphenyl]-2-isopropoxypropanoateYield 73.3%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

24.7 g of Ethyl 3-(3-[(t-butoxycarbonyl)amino]methyl-4-methoxyphenyl)-3-hydroxy-2-isopropoxypropanoate (mixture of erythro form and threo form) was dissolved in 400 ml of trifluoroacetic acid, and 96 ml of triethylsilane was added, and the mixture was stirred for 38 hours. The solvent was evaporated, and the residue was dissolved in 300 ml of 3N hydrochloric acid and 200 ml of hexane. The aqueous layer was washed with 100 ml of hexane, basified with 5N sodium hydroxide solution, and extracted with dichloromethane (200 ml×4). The organic layers were combined and dried over anhydrous magnesium sulfate, to give 13.0 g of the title compound as a pale yellow oil.

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe residue was dissolved in 300 ml of 3N hydrochloric acid
  3. washThe aqueous layer was washed with 100 ml of hexane
  4. extractionextracted with dichloromethane (200 ml×4)
  5. dry with materialdried over anhydrous magnesium sulfate

Sources & evidence

ORD record
ord-b7fbaa7705a34b96870f12d0047104db
Source dataset
uspto-grants-2009_06
Patent number
US07544835B2

Reaction notes

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