HCID 118939147, compound → HCID 118939096, compound

HRID 523993Notes

Reaction equation

HRID 523993 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([O:20]CC3C=CC=CC=3)[C:14]=2[O:18][CH3:19])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>C1COCC1.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([OH:20])[C:14]=2[O:18][CH3:19])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 118939147HCID 118939147, compound

Product 1

HCID 118939096HCID 118939096, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

7.8 g (21 mmol) 6-Benzyloxy-5-methoxy-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester (example XV) in 150 mL THF are hydrogenated (3 bar, r.t.) using 250 mg Pd/C (10%). The reaction mixture is filtered, the solvent is removed in vacuo and the residue is purified by HPLC (ACN/H2O/NH3). After HPLC, ACN is removed in vacuo and the aq. layer is extracted with EtOAc. The organic layer is dried over MgSO4, filtered and the solvent is removed in vacuo.

Workup

  1. custom(3 bar, r.t.)
  2. filtrationThe reaction mixture is filtered
  3. customthe solvent is removed in vacuo
  4. customthe residue is purified by HPLC (ACN/H2O/NH3)
  5. customAfter HPLC, ACN is removed in vacuo
  6. extractionthe aq. layer is extracted with EtOAc
  7. dry with materialThe organic layer is dried over MgSO4
  8. filtrationfiltered
  9. customthe solvent is removed in vacuo

Sources & evidence

ORD record
ord-ff3a2c2111f343edb5180fdfb86ad033
Source dataset
uspto-grants-2016_05
Patent number
US09340510B2

Reaction notes

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