Lithium iodide → HCID 58852305, compound

HRID 1716585Notes

Reaction equation

HRID 1716585 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[CH2:14][C@H:13]([CH2:18]OS(C1C=CC(C)=CC=1)(=O)=O)[CH2:12]2)=[O:7])([CH3:4])([CH3:3])[CH3:2].[I-:30].[Li+]>CN(C=O)C>[C:1]([O:5][C:6](=[O:7])[NH:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[CH2:14][C@H:13]([CH2:18][I:30])[CH2:12]2)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 66321Lithium iodideHCID 86611756HCID 86611756, compound

Product 1

HCID 58852305HCID 58852305, compoundYield 78.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Toluene-4-sulfonic acid (S)-5-tert-butoxycarbonylamino-indan-2-ylmethyl ester (2.93 g, 7.02 mmol) was dissolved in DMF (60 mL) and heated and stirred at 70° C. with lithium iodide (4.7 g, 35.1 mmol) for 18 hours. Volatiles were removed under reduced pressure and the resulting residue was stirred with 100 mL of CH2Cl2 and solids removed by filtration. The filtrate was again evaporated, the residue was purified by flash column chromatography (10% of ethyl ether in hexanes) to yield a white solid as (S)-2-iodomethyl-indan-5-yl-carbamic acid tert-butyl ester (2.05 g, 78.5%).

Workup

  1. temperatureheated
  2. customVolatiles were removed under reduced pressure
  3. customremoved by filtration
  4. customThe filtrate was again evaporated
  5. customthe residue was purified by flash column chromatography (10% of ethyl ether in hexanes)

Sources & evidence

ORD record
ord-3909760885de4f268dbaa3a4edaabdd7
Source dataset
uspto-grants-2010_09
Patent number
US07803816B2

Reaction notes

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