Triacetoxyperiodinane → HCID 118939104, compound

HRID 524012Notes

Reaction equation

HRID 524012 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:17][CH:16]([OH:18])[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([O:19][CH2:20][CH:21]3[CH2:23][CH2:22]3)[CH:14]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl.O>[C:1]([O:5][C:6]([N:8]1[CH2:17][C:16](=[O:18])[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([O:19][CH2:20][CH:21]3[CH2:22][CH2:23]3)[CH:14]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 1179988792(1H)-Isoquinolinecarboxylic acid, 6-(cyclopropylmethoxy)-3,4-dihydro-4-hydroxy-, 1,1-dimethylethyl ester

Product 1

HCID 118939104HCID 118939104, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To 600 mg (1.88 mmol) 6-cyclopropylmethoxy-4-hydroxy-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester (example XLIII.1) in 6 mL DCM are added 825 mg (1.88 mmol) Dess-Martin periodinane and the resulting mixture is stirred at r.t. over night. The reaction mixture is diluted with water and extracted with DCM. The organic layer is concentrated by evaporation and the residue is purified by HPLC (ACN/H2O/HCOOH).

Workup

  1. extractionextracted with DCM
  2. concentrationThe organic layer is concentrated by evaporation
  3. customthe residue is purified by HPLC (ACN/H2O/HCOOH)

Sources & evidence

ORD record
ord-07fd5caed0a544de93aa7e335d7cf2fc
Source dataset
uspto-grants-2016_05
Patent number
US09340510B2

Reaction notes

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