Sodium Hydroxide → HCID 17952314, compound

HRID 1371525Notes

Reaction equation

HRID 1371525 reaction equation
C[O:2][C:3](=[O:17])[CH2:4][CH:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7][N:6]1[CH:14]([CH3:16])[CH3:15].[OH-].[Na+]>CO>[CH:14]([N:6]1[CH2:7][C:8]2[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:5]1[CH2:4][C:3]([OH:17])=[O:2])([CH3:16])[CH3:15]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 69219063Methyl 2,3-dihydro-2-(1-methylethyl)-1H-isoindole-1-acetate

Product 1

HCID 17952314HCID 17952314, compoundYield 85.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To the compound of Step B (0.53 g., 2.30 mmol) in MeOH (5.1 mL) was added 1.0N NaOH (2.53 mL, 2.53 mmol). After two days, the solution was concentrated to dryness. The resulting residue was diluted with 1.0N HCl and water was loaded onto a strong cation exchange resin. The resin was washed with water, THF/water (1:1) and then water. The product was then eluted from the resin with pyridine/water (1:9). The eluent was concentrated to dryness to afford about 0.43 g (85%) of the final compound. EIS-MS 220 [M+1].

Workup

  1. concentrationthe solution was concentrated to dryness
  2. additionThe resulting residue was diluted with 1.0N HCl and water
  3. washThe resin was washed with water, THF/water (1:1)
  4. washThe product was then eluted from the resin with pyridine/water (1:9)
  5. concentrationThe eluent was concentrated to dryness

Sources & evidence

ORD record
ord-8bcb1402882249828d79357509759ef8
Source dataset
uspto-grants-2007_01
Patent number
US07157463B2

Reaction notes

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