HCID 15884739, compound → HCID 15884745, compound

HRID 377162Notes

Reaction equation

HRID 377162 reaction equation
C([NH:8][CH2:9][C:10]([N:12]1[CH2:21][CH:20]([O:22][CH3:23])[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH2:13]1)=[O:11])(OC(C)(C)C)=O>Cl.CCOC(C)=O>[NH2:8][CH2:9][C:10]([N:12]1[CH2:21][CH:20]([O:22][CH3:23])[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH2:13]1)=[O:11]

Participants

4

Reactant 1

HCID 15884739HCID 15884739, compound

Product 1

HCID 15884745HCID 15884745, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of N-(N'-Boc-glycyl)4-methoxy-1,2,3,4-tetrahydroisoquinoline (4.97 g, 16 mmol) in 30 mL of 3 N HCl and 30 mL of EtOAc was heated to reflux for 0.5 hour. The resulting solution was basified to pH 9 and extracted with EtOAc. The aqueous layer was then extracted with 10% iPrOH- CH2Cl2. Drying over MgSO4 of the iPrOH-CH2Cl2 solution and removal of the solvent gave 2.83 g (89%) of N-glycyl4-methoxy-1,2,3,4tetrahydroisoquinoline.

Workup

  1. temperatureto reflux for 0.5 hour
  2. extractionextracted with EtOAc
  3. extractionThe aqueous layer was then extracted with 10% iPrOH- CH2Cl2
  4. dry with materialDrying over MgSO4 of the iPrOH-CH2Cl2 solution and removal of the solvent

Sources & evidence

ORD record
ord-fe5258d8d5334833ab9d34a1fce400c1
Source dataset
uspto-grants-2000_02
Patent number
US06025350

Reaction notes

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