Sodium Hydroxide → 1-[(TERT-BUTOXY)CARBONYL]-2,3-DIHYDRO-1H-INDOLE-5-CARBOXYLIC ACID

HRID 1944543Notes

Reaction equation

HRID 1944543 reaction equation
C[O:2][C:3]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[N:10]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:9][CH2:8]2)=[O:4].[OH-].[Na+]>CO>[C:17]([O:16][C:14]([N:10]1[C:11]2[C:7](=[CH:6][C:5]([C:3]([OH:4])=[O:2])=[CH:13][CH:12]=2)[CH2:8][CH2:9]1)=[O:15])([CH3:20])([CH3:18])[CH3:19]

Participants

4

Reactant 2

HCID 14798Sodium Hydroxide2×HCID 98141901-(1,1-Dimethylethyl) 5-methyl 2,3-dihydro-1H-indole-1,5-dicarboxylate

Product 1

HCID 98784151-[(TERT-BUTOXY)CARBONYL]-2,3-DIHYDRO-1H-INDOLE-5-CARBOXYLIC ACIDYield 69%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 2,3-dihydro-indole-1,5-dicarboxylic acid 1-tert-butyl ester 5-methyl ester (2.3 g, 8.29 mmol) in methanol (30 mL) was treated with 3 N aqueous sodium hydroxide (2.77 mL, 8.29 mmol) and heated at reflux for 4 hours. An additional portion of 3N aqueous sodium hydroxide (1.38 mL, 4.14 mmol) was added and the solution was heated at reflux for an additional 28 hours. The solution was concentrated in vacuo and then diluted with water. The resultant solution was neutralized with 2N hydrochloric acid (6.3 mL). The product precipitated and was collected by filtration and washed with water, to give the product 1.5 g (69%). 1H NMR (DMSO-d6): δ 1.51 (s, 9 H), 3.10 (t, 2 H), 3.95 (t, 2 H), 7.53-7.82 (m, 3 H) and 12.59 (s, 1 H).

Workup

  1. temperatureheated
  2. temperatureat reflux for 4 hours
  3. temperaturethe solution was heated
  4. temperatureat reflux for an additional 28 hours
  5. concentrationThe solution was concentrated in vacuo
  6. additiondiluted with water
  7. customThe product precipitated
  8. filtrationwas collected by filtration
  9. washwashed with water

Sources & evidence

ORD record
ord-851d18fa98e84c50aa1176a0a461e4c3
Source dataset
uspto-grants-2013_03
Patent number
US08394828B2

Reaction notes

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