Lithium Hydroxide → 5-(6-Methylpyrazine-2-carboxamido)bicyclo[3.2.1]octane-1-carboxylic acid

HRID 1408866Notes

Reaction equation

HRID 1408866 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([C:8]([NH:10][C:11]23[CH2:18][C:15]([C:19]([O:21]C)=[O:20])([CH2:16][CH2:17]2)[CH2:14][CH2:13][CH2:12]3)=[O:9])[CH:5]=[N:4][CH:3]=1.[Li+].[OH-]>CO.O>[CH3:1][C:2]1[N:7]=[C:6]([C:8]([NH:10][C:11]23[CH2:18][C:15]([C:19]([OH:21])=[O:20])([CH2:16][CH2:17]2)[CH2:14][CH2:13][CH2:12]3)=[O:9])[CH:5]=[N:4][CH:3]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 68048079Methyl 5-(6-methylpyrazine-2-carboxamido)bicyclo[3.2.1]octane-1-carboxylate

Product 1

HCID 679810305-(6-Methylpyrazine-2-carboxamido)bicyclo[3.2.1]octane-1-carboxylic acidYield 91.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of methyl 5-(6-methylpyrazine-2-carboxamido)bicyclo[3.2.1]octane-1-carboxylate (1.28 g, 4.21 mmol) and LiOH (0.15 g, 6.25 mmol) in methanol (30 mL) and H2O (3 mL) was refluxed for two hours. After cooled to room temperature, methanol was removed under reduced pressure. The residue was partitioned between water (50 mL) and diethyl ether (50 mL) to remove organic impurities. The aqueous phase was adjusted to pH 1˜2 with 2N aq. HCl and then extracted with dichloromethane (3×50 mL). The combined organic layer was washed with water (50 mL) and brine (50 mL), dried over Na2SO4 and concentrated under reduced pressure to afford 1.11 g (91%) of 5-(6-methylpyrazine-2-carboxamido)bicyclo[3.2.1]octane-1-carboxylic acid as a white solid. ESI-MS m/z: 290 (M+H)+.

Workup

  1. custommethanol was removed under reduced pressure
  2. customThe residue was partitioned between water (50 mL) and diethyl ether (50 mL)
  3. customto remove organic impurities
  4. extractionextracted with dichloromethane (3×50 mL)
  5. washThe combined organic layer was washed with water (50 mL) and brine (50 mL)
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6bf1bcf7259d436c86422b566b9dcfe7
Source dataset
uspto-grants-2014_12
Patent number
US08921370B2

Reaction notes

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