Iometopane → 3b-(4-Iodophenyl)tropane-2b-carboxylic

HRID 1419661Notes

Reaction equation

HRID 1419661 reaction equation
[C:1]([C@H:5]1[C@@H:11]([C:12]2[CH:17]=[CH:16][C:15]([I:18])=[CH:14][CH:13]=2)[CH2:10][C@H:9]2[N:19]([CH3:20])[C@@H:6]1[CH2:7][CH2:8]2)([O:3]C)=[O:2]>O.O1CCOCC1>[C:1]([C@H:5]1[C@@H:11]([C:12]2[CH:13]=[CH:14][C:15]([I:18])=[CH:16][CH:17]=2)[CH2:10][C@H:9]2[N:19]([CH3:20])[C@@H:6]1[CH2:7][CH2:8]2)([OH:3])=[O:2]

Participants

3

Reactant 1

HCID 108220Iometopane

Product 1

HCID 156397973b-(4-Iodophenyl)tropane-2b-carboxylic

Reagents, catalysts & solvents 1

HCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

A round bottom flask filled with a solution of 100 mg of 2β-Carbomethoxy-3β-(4-Iodophenyl)tropane in 10 mL of 1:1 water/dioxane was heated to a gentle reflux for two days. The solvent was then removed and the white residue was triturated with hot ethyl acetate twice. The remaining solid was dried under in vacuo to yield 90 mg of CIT-acid 7, (93%) as a white solid.

Workup

  1. temperaturewas heated to
  2. temperaturea gentle reflux for two days
  3. customThe solvent was then removed
  4. customthe white residue was triturated with hot ethyl acetate twice
  5. customThe remaining solid was dried under in vacuo
  6. customto yield 90 mg of CIT-acid 7, (93%) as a white solid

Sources & evidence

ORD record
ord-df1fc272bc504d0c9138a3f71a3f28ec
Source dataset
uspto-grants-1999_03
Patent number
US05888475

Reaction notes

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