Iodine → 7-(2-iodoethyl)-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester

HRID 564051Notes

Reaction equation

HRID 564051 reaction equation
[I:1]I.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N1C=CC=CC=1.[C:28]([O:32][C:33]([N:35]1[CH2:44][CH2:43][C:42]2[C:37](=[CH:38][C:39]([CH2:45][CH2:46]O)=[CH:40][CH:41]=2)[CH2:36]1)=[O:34])([CH3:31])([CH3:30])[CH3:29]>C1(C)C=CC=CC=1>[C:28]([O:32][C:33]([N:35]1[CH2:44][CH2:43][C:42]2[C:37](=[CH:38][C:39]([CH2:45][CH2:46][I:1])=[CH:40][CH:41]=2)[CH2:36]1)=[O:34])([CH3:31])([CH3:30])[CH3:29]

Participants

6

Reactant 4

HCID 807IodineHCID 1049PyridineHCID 11776TriphenylphosphineHCID 670071427-(2-Hydroxy-ethyl)-3,4-dihydro-1H-isoquinoline-2-carboxylic Acid Tert-Butyl Ester

Product 1

HCID 580428517-(2-iodoethyl)-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To 1.21 g (4.76 mmol) iodine in 50 mL toluene is added 1.59 g (4.76 mmol) polymer bound triphenyl-phosphane. The mixture is stirred 5 min at RT and then 0.80 mL (9.92 mmol) pyridine and 1.10 g (3.97 mmol) 7-(2-hydroxy-ethyl)-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester (preparation 7c) is added. The reaction mixture is stirred 5 h at 90° C., is cooled to RT and is filtered. The filtrate is washed with saturated aqueous sodium thiosulfate-solution, brine and dried over MgSO4. After filtration and evaporation of the solvent, the residue is purified via chromatography (silica gel; PE/EtOAc=9:1).

Workup

  1. stirringThe reaction mixture is stirred 5 h at 90° C.
  2. temperatureis cooled to RT
  3. filtrationis filtered
  4. washThe filtrate is washed with saturated aqueous sodium thiosulfate-solution, brine
  5. dry with materialdried over MgSO4
  6. filtrationAfter filtration and evaporation of the solvent
  7. customthe residue is purified via chromatography (silica gel; PE/EtOAc=9:1)

Sources & evidence

ORD record
ord-a5b696992c8443efa961831f5cf5c384
Source dataset
uspto-grants-2011_11
Patent number
US08067590B2

Reaction notes

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