Trimethylsilyl iodide → HCID 22312334, compound

HRID 860199Notes

Reaction equation

HRID 860199 reaction equation
COC([NH:5][CH:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:9][NH:8][C:7]1=[O:16])=O.[CH3:17][Si](I)(C)C>C(#N)C.C(OCC)(=O)C>[NH2:5][CH:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:9][N:8]([CH3:17])[C:7]1=[O:16]

Participants

5

Reactant 2

HCID 85247Trimethylsilyl iodideHCID 12593302HCID 12593302, compound

Product 1

HCID 22312334HCID 22312334, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

Step D—Removal of the Methoxyoxycarbonyl Group (MOC): To the 4-methoxycarbonylamino-1,2,3,4-tetrahydroisoquinoline-3-one (3.4 mmoles) in 30 mL of acetonitrile was added 2 mole equivalents of trimethylsilyliodide (TMSI). The reaction mixture was heated to 50–80° C. for 3 hrs and then cooled and poured into a seperatory funnel. The reaction mixture was diluted with ethyl acetate and washed with 1 molar K2CO3 and then with 5% NaHSO3. The organic layer was dried over Na2SO4 and filtered. The solvent was removed under reduced pressure to give the 4-amino-1,2,3,4-tetrahydroisoquinoline-3-one derivative. Typical yields range from 50–87%.

Workup

  1. temperatureThe reaction mixture was heated to 50–80° C. for 3 hrs
  2. temperaturecooled
  3. additionpoured into a seperatory funnel
  4. washwashed with 1 molar K2CO3
  5. dry with materialThe organic layer was dried over Na2SO4
  6. filtrationfiltered
  7. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-92281e3b17f8412faa90cb15593141c9
Source dataset
uspto-grants-2006_12
Patent number
US07153847B2

Reaction notes

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