Hydrogen chloride-ethyl acetate → 1-cyclohexyl-2-L-prolyl-1,2,3,4-tetrahydroisoquinoline

HRID 2383018Notes

Reaction equation

HRID 2383018 reaction equation
Cl.CCOC(C)=O.[CH:8]1([CH:14]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH2:17][CH2:16][N:15]2[C:24]([C@@H:26]2[CH2:30][CH2:29][CH2:28][N:27]2C(OC(C)(C)C)=O)=[O:25])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1>CCOC(C)=O>[CH:8]1([CH:14]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH2:17][CH2:16][N:15]2[C:24](=[O:25])[C@@H:26]2[CH2:30][CH2:29][CH2:28][NH:27]2)[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]1

Participants

4

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 68250501tert-butyl (2S)-2-[(1-cyclohexyl-3,4-dihydroisoquinolin-2(1H)-yl)carbonyl]pyrrolidine-1-carboxylate

Product 1

HCID 593966061-cyclohexyl-2-L-prolyl-1,2,3,4-tetrahydroisoquinolineYield 92.9%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

4 M HCl/EtOAc (4 mL) was added to a solution of tert-butyl (2S)-2-[(1-cyclohexyl-3,4-dihydroisoquinolin-2(1H)-yl)carbonyl]pyrrolidine-1-carboxylate (1.79 g) in EtOAc (4 mL). The mixture was stirred at room temperature for 5 hours. The solvent was evaporated under reduced pressure, and chloroform and a saturated aqueous sodium hydrogen carbonate solution were added to the residue. The organic layer was washed with saturated brine, dried over magnesium sulfate, filtered, and concentrated to obtain 1-cyclohexyl-2-L-prolyl-1,2,3,4-tetrahydroisoquinoline (1.26 g).

Workup

  1. customThe solvent was evaporated under reduced pressure, and chloroform
  2. additiona saturated aqueous sodium hydrogen carbonate solution were added to the residue
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-03916f6bf25d4fabb973988dab1d5de6
Source dataset
uspto-grants-2012_09
Patent number
US08263607B2

Reaction notes

Loading…