Lithium Hydroxide → HCID 83669226, compound

HRID 518581Notes

Reaction equation

HRID 518581 reaction equation
[Li+].[OH-].[C:3]1([C:12]([O:14]CC)=[O:13])[C:8]2[CH2:9][CH2:10][CH2:11][C:7]=2[CH:6]=[CH:5][N:4]=1>O.CO>[C:3]1([C:12]([OH:14])=[O:13])[C:8]2[CH2:9][CH2:10][CH2:11][C:7]=2[CH:6]=[CH:5][N:4]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 450986655H-Cyclopenta[c]pyridine-1-carboxylicacid,6,7-dihydro-,ethylester(9CI)

Product 1

HCID 83669226HCID 83669226, compoundYield 63.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent

Procedure

A 2N solution of LiOH (50 mL) in water was slowly added to the title compound of step 1 (10 g, 52.4 mmol) in MeOH (250 mL) at 0° C. The mixture was allowed to warm to rt and stirred for 30 min. The MeOH was reduced under vacuum and the residual aqueous solution was washed with EtOAc. The organic phase was re-extracted with water. The combined aqueous extracts were acidified to pH=2 with 1N HCl. The water was removed and preparative HPLC gave the title compound (5.4 g, 63%) as a white solid. 1H NMR (CD3OD, 400 MHz): δ 8.45 (d, J=5.6 Hz, 1H), 7.88 (d, J=5.6 Hz, 1H), 3.39 (t, J=8.0, 7.6 Hz, 2H), 3.16 (d, t, J=8.0, 7.6 Hz, 2H), 2.16-2.20 (m, 2H).

Workup

  1. washthe residual aqueous solution was washed with EtOAc
  2. extractionThe organic phase was re-extracted with water
  3. customThe water was removed

Sources & evidence

ORD record
ord-4ef16cc474754dd1840159a1db992fa3
Source dataset
uspto-grants-2015_08
Patent number
US09115114B2

Reaction notes

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