Ethanol hydrochloride → ethyl (S)-3-(2-amino-1,2,3,4-tetrahydronaphthalen-7-yl)acrylate

HRID 369361Notes

Reaction equation

HRID 369361 reaction equation
C(OC([NH:8][C@H:9]1[CH2:18][CH2:17][C:16]2[C:11](=[CH:12][C:13]([CH:19]=[CH:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:14][CH:15]=2)[CH2:10]1)=O)(C)(C)C.C(O)C.Cl>C(O)C>[NH2:8][C@H:9]1[CH2:18][CH2:17][C:16]2[C:11](=[CH:12][C:13]([CH:19]=[CH:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:14][CH:15]=2)[CH2:10]1

Participants

4

Reactant 2

HCID 21887872Ethanol hydrochlorideHCID 57134535ethyl (S)-3-[2-(tert-butoxycarbonylamino)-1,2,3,4-tetrahydronaphthalen-7-yl]acrylate

Product 1

HCID 53659126ethyl (S)-3-(2-amino-1,2,3,4-tetrahydronaphthalen-7-yl)acrylateYield 99.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl (S)-3-[2-(tert-butoxycarbonylamino)-1,2,3,4-tetrahydronaphthalen-7-yl]acrylate (516 mg) was dissolved in ethanol (10 ml), and 3 M hydrogen chloride ethanol solution (2 ml) was added to the solution at room temperature with stirring. After reaction for 13 hours, the reaction mixture was concentrated in vacuo. A saturated aqueous sodium bicarbonate solution (20 ml) and dichloromethane (5 ml) were added to the residue, and the resulting mixture was stirred for an hour at room temperature. Water was added to the reaction mixture, and the resulting mixture was extracted with dichloromethane. The extract was washed with water and dried over anhydrous magnesium sulfate. Removal of the solvent in vacuo gave ethyl (S)-3-(2-amino-1,2,3,4-tetrahydronaphthalen-7-yl)acrylate (366 mg) as an oil.

Workup

  1. customAfter reaction for 13 hours
  2. concentrationthe reaction mixture was concentrated in vacuo
  3. additionA saturated aqueous sodium bicarbonate solution (20 ml) and dichloromethane (5 ml) were added to the residue
  4. stirringthe resulting mixture was stirred for an hour at room temperature
  5. additionWater was added to the reaction mixture
  6. extractionthe resulting mixture was extracted with dichloromethane
  7. washThe extract was washed with water
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customRemoval of the solvent in vacuo

Sources & evidence

ORD record
ord-c1d10ad407be453493250bc57fc47020
Source dataset
uspto-grants-2000_10
Patent number
US06136852

Reaction notes

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