Triacetoxyperiodinane → HCID 118939142, compound

HRID 524009Notes

Reaction equation

HRID 524009 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][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH: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][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH:14]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 118939106HCID 118939106, compound

Product 1

HCID 118939142HCID 118939142, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To 500 mg (1.41 mmol) 6-benzyloxy-4-hydroxy-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester (example XL) in 8 mL DCM are added 618 mg (1.41 mmol) Dess-Martin periodinane and stirred at r.t. over night. After that time, 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-54c72737d3ae4065b8e72db466882ccc
Source dataset
uspto-grants-2016_05
Patent number
US09340510B2

Reaction notes

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