Acetic Acid → 1H-Isoindole-1-carboxylic acid, 2,3-dihydro-, Methyl ester, hydrochloride

HRID 2164219Notes

Reaction equation

HRID 2164219 reaction equation
[ClH:1].[CH:2]1([C:11]([OH:13])=[O:12])[CH:10]2[CH:5]([CH2:6][CH2:7][CH2:8][CH2:9]2)[CH2:4][NH:3]1.[C:14](O)(=O)C.[CH3:18]COCC>CO.[Rh]>[ClH:1].[CH:2]1([C:11]([O:13][CH3:14])=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][NH:3]1.[ClH:1].[CH:2]1([C:11]([O:13][CH3:18])=[O:12])[CH:10]2[CH:5]([CH2:6][CH2:7][CH2:8][CH2:9]2)[CH2:4][NH:3]1

Participants

7

Reactant 3

HCID 176Acetic AcidHCID 3283Diethyl EtherHCID 70083948HCID 70083948, compound

Product 2

HCID 122789231H-Isoindole-1-carboxylic acid, 2,3-dihydro-, Methyl ester, hydrochlorideHCID 20405955HCID 20405955, compound

Reagents, catalysts & solvents 2

HCID 23948RhodiumCatalystHCID 887MethanolSolvent

Procedure

Octahydro-1H-isoindole-1-carboxylic acid hydrochloride used as an intermediate in this preparation is obtained by the following method. Following a procedure given in Gazz. Chim. Ital, 106, 65(1976), 2,3-dihydro-1H-isoindole-1-carboxylic acid, methyl ester, hydrochloride is prepared. This compound, 2.14 g, is dissolved in 100 ml of methanol and 5 ml of acetic acid and hydrogenated over 0.5 g of 10% rhodium/carbon catalyst. The catalyst is removed by filtration and the filtrate is concentrated to give a residue which solidifies on trituration with ether. Recrystallization from methanol-ether gives a pure sample of methyl octahydro-1H-isoindole-1-carboxylate hydrochloride, mp 181°-183° C.

Workup

  1. customis obtained by the following method
  2. customThe catalyst is removed by filtration
  3. concentrationthe filtrate is concentrated
  4. customto give a residue which
  5. customRecrystallization from methanol-ether

Sources & evidence

ORD record
ord-e4b7cfefe94b495a964fd0b2dab6408f
Source dataset
uspto-grants-1985_03
Patent number
US04503043

Reaction notes

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