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

HRID 627015Notes

Reaction equation

HRID 627015 reaction equation
[N:1]1([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[CH2:3][CH:2]1[C:10]([O:12]CC)=[O:11].CO.[Li+:24].[OH-]>C1COCC1>[C:18]([O:17][C:15]([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:16])([CH3:21])([CH3:19])[CH3:20].[Li+:24]

Participants

5

Reactant 3

HCID 887MethanolHCID 3939Lithium HydroxideHCID 691087141-tert-butyl 2-ethyl 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 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-tert-butyl 2-ethyl 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) (200 mg, 684 μmol, Eq: 1.00) in THF (1.2 mL) and MeOH (0.8 mL) was added LiOH (16.4 mg, 684 μmol, Eq: 1.00) in one portion. The reaction mixture was stirred at rt for 72 h. The reaction mixture was concentrated in vacuo and the residue treated with DCM (10 mL) to give lithium 1-(tert-butoxycarbonyl)-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine-2-carboxylate as an off-white solid (200 mg) which was used without further purification.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additionthe residue treated with DCM (10 mL)

Sources & evidence

ORD record
ord-a1212a436ae746ca8ee1a93a798deef3
Source dataset
uspto-grants-2016_04
Patent number
US09309248B2

Reaction notes

Loading…