Lithium Hydroxide → 1017436-19-9

HRID 887133Notes

Reaction equation

HRID 887133 reaction equation
[O:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.[Li+].[OH-].ClC1[N:14]=[C:13]2[CH:15]([C:18]([O:20]C)=[O:19])[CH2:16][CH2:17]C2=CC=1>CO>[O:1]=[C:5]1[NH:14][C:13]2[CH:15]([C:18]([OH:20])=[O:19])[CH2:16][CH2:17][C:2]=2[CH:3]=[CH:4]1

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 57907634HCID 57907634, compound

Product 1

HCID 242717621017436-19-9Yield 90%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a 15 mL mixture of tetrahydrofuran, methanol, and a 1.0 N aqueous LiOH solution in a 3:1:1 ratio was added 0.242 g (1.14 mmol) of methyl 2-chloro-6,7-dihydro-5H-cyclopenta[b]pyridine-7-carboxylate from Step C above. The resulting mixture was stirred at ambient temperature for 1 h. The solution was evaporated in vacuo and the resulting light brown residue was purified by reverse phase HPLC (YMC Pack Pro C18, 100×20 mm I.D. column, 0-60% 0.01% trifluoroacetic acid in acetonitrile/0.01% trifluoroacetic acid in water gradient) to give the title compound as a brown oil (184 mg, 90%). LC-MS: m/z (E/S) 180.0 (MH)+.

Workup

  1. customThe solution was evaporated in vacuo
  2. customthe resulting light brown residue was purified by reverse phase HPLC (YMC Pack Pro C18, 100×20 mm I.D. column, 0-60% 0.01% trifluoroacetic acid in acetonitrile/0.01% trifluoroacetic acid in water gradient)

Sources & evidence

ORD record
ord-f972c714e42f405bb7d09f82687944c1
Source dataset
uspto-grants-2012_08
Patent number
US08247415B2

Reaction notes

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