Lithium Hydroxide → HCID 117885717, compound

HRID 627030Notes

Reaction equation

HRID 627030 reaction equation
[CH3:1][CH:2]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][CH:9]=2)[N:4]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH:3]1[C:18]([O:20]CC)=[O:19].C1COCC1.[Li+].[OH-].OS([O-])(=O)=O.[K+]>C(O)C>[C:14]([O:13][C:11]([N:4]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:10]2[CH:2]([CH3:1])[CH:3]1[C:18]([OH:20])=[O:19])=[O:12])([CH3:15])([CH3:16])[CH3:17]

Participants

6

Reactant 4

HCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 516920Potassium bisulfateHCID 118380527HCID 118380527, compound

Product 1

HCID 117885717HCID 117885717, compoundYield 48.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In a 100 mL round-bottomed flask, 1-tert-butyl 2-ethyl 3-methyl-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine-1,2-dicarboxylate (235 mg, 767 μmol, Eq: 1.00) was combined with THF (7.0 mL) and ethanol (2.3 mL) to give a colorless suspension. 1 M aqueous LiOH (2.3 mL, 2.3 mmol, Eq: 3) was added and the reaction was stirred at rt for 7 d. 0.1 M Aqueous KHSO4 was added and the resulting mixture was extracted with DCM (50 mL×3). The combined organic layers were dried over Na2SO4 and concentrated in vacuo to give 3-methyl-2,3-dihydro-pyrrolo[2,3-b]pyridine-1,2-dicarboxylic acid 1-tert-butyl ester (103 mg), m/z=277.

Workup

  1. customto give a colorless suspension
  2. extractionthe resulting mixture was extracted with DCM (50 mL×3)
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-44571ea4154e47b99ee1db74fdd15a40
Source dataset
uspto-grants-2016_04
Patent number
US09309248B2

Reaction notes

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