Lithium hydroxide, monohydrate → HCID 69003416, compound

HRID 1987990Notes

Reaction equation

HRID 1987990 reaction equation
[N:1]12[CH2:8][CH2:7][C:4]([C:9]3[O:10][C:11]4[C:12](=[C:14]([C:18]([O:20]C)=[O:19])[CH:15]=[CH:16][CH:17]=4)[N:13]=3)([CH2:5][CH2:6]1)[CH2:3][CH2:2]2.O.[OH-].[Li+]>C1COCC1.O>[N:1]12[CH2:2][CH2:3][C:4]([C:9]3[O:10][C:11]4[C:12](=[C:14]([C:18]([OH:20])=[O:19])[CH:15]=[CH:16][CH:17]=4)[N:13]=3)([CH2:7][CH2:8]1)[CH2:5][CH2:6]2

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 68996784HCID 68996784, compound

Product 1

HCID 69003416HCID 69003416, compoundYield 108.8%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

A mixture of methyl 2-(quinuclidin-4-yl)benzoxazole-4-carboxylate (233 mg, 0.81 mmol), lithium hydroxide monohydrate (51 mg, 1.22 mmol) and THF/water (2:1, 15 mL) was stirred at room temperature for 6 h. The reaction mixture was concentrated, and washed with brine (10 mL), the precipitate which formed was filtered, washed with hexanes and dried to afford 2-(quinuclidin-4-yl)benzoxazole-4-carboxylic acid (240 mg, 108%) as a brown solid: 1H NMR (500 MHz, DMSO-d6) δ 7.80 (d, J=8.0 Hz, 1H), 7.67 (d, J=8.0 Hz, 1H), 7.31 (d, J=8.0 Hz, 1H), 2.83-2.81 (m, 6H), 1.89-1.84 (m, 6H); MS (ESI+) m/z 273 (M+H).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. washwashed with brine (10 mL)
  3. customthe precipitate which formed
  4. filtrationwas filtered
  5. washwashed with hexanes
  6. customdried

Sources & evidence

ORD record
ord-e7d69b256ade44e6b3398a2bbf39e2cc
Source dataset
uspto-grants-2009_06
Patent number
US07553846B2

Reaction notes

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