Lithium hydroxide, monohydrate → 6-(Adamantan-1-ylmethoxy)-5-cyclopropylnicotinic acid

HRID 1849581Notes

Reaction equation

HRID 1849581 reaction equation
[C:1]12([CH2:11][O:12][C:13]3[C:22]([CH:23]4[CH2:25][CH2:24]4)=[CH:21][C:16]([C:17]([O:19]C)=[O:18])=[CH:15][N:14]=3)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.O.[OH-].[Li+]>O1CCCC1.O.C(OCC)(=O)C>[C:1]12([CH2:11][O:12][C:13]3[C:22]([CH:23]4[CH2:25][CH2:24]4)=[CH:21][C:16]([C:17]([OH:19])=[O:18])=[CH:15][N:14]=3)[CH2:8][CH:7]3[CH2:9][CH:3]([CH2:4][CH:5]([CH2:6]3)[CH2:10]1)[CH2:2]2

Participants

6

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 86702923Methyl 6-(adamantan-1-ylmethoxy)-5-cyclopropylnicotinate

Product 1

HCID 867029246-(Adamantan-1-ylmethoxy)-5-cyclopropylnicotinic acid

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of methyl 6-(adamantan-1-ylmethoxy)-5-cyclopropylnicotinate (1.17 g, 3.43 mmol) and lithium hydroxide monohydrate (0.58 g, 13.70 mmol) in tetrahydrofuran (60 mL) and water (10 mL) was refluxed for 2 h. The reaction mixture was cooled to ambient temperature and diluted with ethyl acetate (100 mL); washed with 1 M aqueous hydrochloric acid (80 mL) and brine (80 mL); dried over anhydrous sodium sulfate; filtered and concentrated in vacuo to afford the title compound which was used without further characterization. MS (ES+) m/z: 328.2 (M+H).

Workup

  1. temperaturewas refluxed for 2 h
  2. washwashed with 1 M aqueous hydrochloric acid (80 mL) and brine (80 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-985115fec0fe451f869d9d27561acb52
Source dataset
uspto-grants-2015_02
Patent number
US08952169B2

Reaction notes

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