Lithium hydroxide, monohydrate → HCID 69134660, compound

HRID 456750Notes

Reaction equation

HRID 456750 reaction equation
[C:1]([C@@H:3]1[CH2:7][CH2:6][CH2:5][N:4]1[C:8]([C@@H:10]1[C@H:15]2[CH2:16][C@H:12]([C@H:13]([O:17][CH2:18][C:19]([O:21]CC)=[O:20])[CH2:14]2)[N:11]1[C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])=[O:9])#[N:2].O.[OH-].[Li+]>O1CCOCC1.O>[C:27]([O:26][C:24]([N:11]1[C@H:10]([C:8]([N:4]2[CH2:5][CH2:6][CH2:7][C@H:3]2[C:1]#[N:2])=[O:9])[C@H:15]2[CH2:16][C@@H:12]1[C@H:13]([O:17][CH2:18][C:19]([OH:21])=[O:20])[CH2:14]2)=[O:25])([CH3:30])([CH3:28])[CH3:29]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 86598903HCID 86598903, compound

Product 1

HCID 69134660HCID 69134660, compoundYield 112.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of tert-butyl (1R,3S,4S,6R)-3-{[(2S)-2-cyano-1-pyrrolidinyl]carbonyl}-6-(2-ethoxy-2-oxoethoxy)-2-azabicyclo[2.2.1]heptane-2-carboxylate obtained in Example 15-1 (249 mg) in dioxane (3 mL) and water (1 mL), was added lithium hydroxide monohydrate (302 mg). The mixture was stirred at room temperature for 1 hr. The resulting mixture was evaporated in vacuo. 1N Hydrochloric acid (1.2 mL) was added to the residue, and the mixture was extracted with ethyl acetate. The combined organic phase was washed with brine, dried over sodium sulfate, and evaporated in vacuo to give the target compound (261 mg).

Workup

  1. customThe resulting mixture was evaporated in vacuo
  2. addition1N Hydrochloric acid (1.2 mL) was added to the residue
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe combined organic phase was washed with brine
  5. dry with materialdried over sodium sulfate
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-e20d2f45f6424cab8742919745ae89c6
Source dataset
uspto-grants-2007_03
Patent number
US07186731B2

Reaction notes

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