Sodium Hydroxide → 2-(tert-Butoxycarbonyl)-2,3-dihydro-1H-isoindole-5-carboxylic acid

HRID 268711Notes

Reaction equation

HRID 268711 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([C:17]([O:19]C)=[O:18])[CH:14]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>CO>[C:1]([O:5][C:6]([N:8]1[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([C:17]([OH:19])=[O:18])[CH:14]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 179863022-Tert-butyl 5-methyl isoindoline-2,5-dicarboxylate

Product 1

HCID 164501432-(tert-Butoxycarbonyl)-2,3-dihydro-1H-isoindole-5-carboxylic acidYield 73.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

A solution of N-t-butoxycarbonyl-5-methoxycarbonylisoindoline (D12) (2.11 g) in MeOH (10 ml) was treated with 1M NaOH and heated at 60° C. for 1 h. The mixture was cooled to rt and the MeOH evaporated. The aqueous was washed with diethyl ether (2×20 ml), then acidified with 5% citric acid solution and extracted with diethyl ether (2×20 ml). The combined extracts were washed with water (2×20 ml), brine (20 ml), dried (MgSO4) and evaporated to give the title compound (D13) (1.47 g). MS electrospray (+ion) 264 (MH+). 1H NMR δ (CDCl3): 8.02 (2H, m), 7.35 (1H, m), 4.75 (2H, s), 4.71 (2H, s), 1.53 (9H, s).

Workup

  1. temperatureThe mixture was cooled to rt
  2. customthe MeOH evaporated
  3. washThe aqueous was washed with diethyl ether (2×20 ml)
  4. extractionextracted with diethyl ether (2×20 ml)
  5. washThe combined extracts were washed with water (2×20 ml), brine (20 ml)
  6. dry with materialdried (MgSO4)
  7. customevaporated

Sources & evidence

ORD record
ord-434cd512a41c45eeab9ee540ccda077a
Source dataset
uspto-grants-2008_11
Patent number
US07446103B2

Reaction notes

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