Tetrahydrofuran → lithium 1-(tert-butoxycarbonyl)-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine-2-carboxylate

HRID 627012Notes

Reaction equation

HRID 627012 reaction equation
[N:1]1([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[CH2:3][CH:2]1[C:10]([O:12]C)=[O:11].C1COCC1.O.[OH-].[Li+:28]>CO>[C:17]([O:16][C:14]([N:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[CH2:3][CH:2]1[C:10]([O-:12])=[O:11])=[O:15])([CH3:20])([CH3:18])[CH3:19].[Li+:28]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 1183805211-tert-butyl 2-methyl 2,3-dihydro-1H-pyrrolo[2,3-b]pyridine-1,2-dicarboxylate

Product 1

HCID 118380491lithium 1-(tert-butoxycarbonyl)-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine-2-carboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In a 250 mL round-bottomed flask, 1-tert-butyl 2-methyl 2,3-dihydro-1H-pyrrolo[2,3-b]pyridine-1,2-dicarboxylate (prepared using methods of M Boehringer, et al. U.S. Pat. No. 7,417,144) (3.0 g, 10.8 mmol, Eq: 1.00) was combined with THF (18 mL) and MeOH (12 mL) to give a colorless solution. Lithium hydroxide monohydrate (452 mg, 10.8 mmol, Eq: 1.00) was added and the reaction was stirred at rt overnight. The crude reaction mixture was concentrated in vacuo to give lithium 1-(tert-butoxycarbonyl)-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine-2-carboxylate as an off-white solid (2.9 g), m/z=265 (M+H).

Workup

  1. customto give a colorless solution
  2. customThe crude reaction mixture
  3. concentrationwas concentrated in vacuo

Sources & evidence

ORD record
ord-b9f9e0848eee4b9298c2929dd8b45fcc
Source dataset
uspto-grants-2016_04
Patent number
US09309248B2

Reaction notes

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