Sodium Hydroxide → 2-t-butoxycarbonyl-9-carboxymethyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole

HRID 2301086Notes

Reaction equation

HRID 2301086 reaction equation
[OH-].[Na+].[C:3]([O:7][C:8]([N:10]1[CH2:22][CH2:21][C:20]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[N:13]([CH2:23][C:24]([O:26]C)=[O:25])[C:12]=2[CH2:11]1)=[O:9])([CH3:6])([CH3:5])[CH3:4]>CO>[C:3]([O:7][C:8]([N:10]1[CH2:22][CH2:21][C:20]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[N:13]([CH2:23][C:24]([OH:26])=[O:25])[C:12]=2[CH2:11]1)=[O:9])([CH3:6])([CH3:4])[CH3:5]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 110784542-Tert-butoxycarbonyl-9-methoxycarbonylmethyl-1,2,3,4-tetrahydropyrido[3,4-b]indole

Product 1

HCID 183773592-t-butoxycarbonyl-9-carboxymethyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indoleYield 74.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methanol (100 ml) and sodium hydroxide solution (1 N, 22 mmol) were added to 2-t-butoxycarbonyl-9-methoxycarbonylmethyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole (7.42 g, 21.5 mmol) and stirred at room temperature for 2 hours, the solvent was removed by evaporation under a reduced pressure, the thus obtained oily material was dissolved in ethyl acetate (100 ml) and then the ethyl acetate layer was washed with water, dried with anhydrous sodium sulfate and concentrated under a reduced pressure. The resulting residue was precipitated by adding diisopropyl ether (30 ml), thereby obtaining 5.29 g (16.0 mmol, 74.4% in yield) of 2-t-butoxycarbonyl-9-carboxymethyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole.

Workup

  1. customthe solvent was removed by evaporation under a reduced pressure
  2. dissolutionthe thus obtained oily material was dissolved in ethyl acetate (100 ml)
  3. washthe ethyl acetate layer was washed with water
  4. dry with materialdried with anhydrous sodium sulfate
  5. concentrationconcentrated under a reduced pressure
  6. customThe resulting residue was precipitated
  7. additionby adding diisopropyl ether (30 ml)

Sources & evidence

ORD record
ord-d141a53d123642d1aa871e96cf561a77
Source dataset
uspto-grants-2002_12
Patent number
US06498251B1

Reaction notes

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