Water → 2H-Isoindole-2-carboxylic acid, 1,3-dihydro-4-(hydroxymethyl)-, 1,1-dimethylethyl ester

HRID 1396670Notes

Reaction equation

HRID 1396670 reaction equation
[CH:1]([C:3]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:4]=1[CH2:5][N:6]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:7]2)=[O:2].[BH4-].[Na+].O.C(OCC)(=O)C>CO>[OH:2][CH2:1][C:3]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:4]=1[CH2:5][N:6]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:7]2

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 4311764Sodium borohydrideHCID 509991201,1-Dimethylethyl 4-formyl-1,3-dihydro-2H-isoindole-2-carboxylate

Product 1

HCID 574156602H-Isoindole-2-carboxylic acid, 1,3-dihydro-4-(hydroxymethyl)-, 1,1-dimethylethyl esterYield 60.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 350 mg of tert-butyl 4-formyl-1,3-dihydro-2H-isoindole-2-carboxylate in 11 mL of methanol was added 134 mg of sodium borohydride under ice-cooling, followed by stirring at room temperature overnight. To the reaction mixture were added water and ethyl acetate and the aqueous layer was separated. The obtained organic layer was washed with saturated brine and then dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to obtain 213 mg of tert-butyl 4-(hydroxymethyl)-1,3-dihydro-2H-isoindole-2-carboxylate as a yellow oil.

Workup

  1. temperaturecooling
  2. customthe aqueous layer was separated
  3. washThe obtained organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-86c0a631d5334e07b102f965f6befacb
Source dataset
uspto-grants-2014_12
Patent number
US08901126B2

Reaction notes

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