Lithium Hydroxide → HCID 178511260, compound

HRID 643454Notes

Reaction equation

HRID 643454 reaction equation
[C:1]([C@H:3]1[CH2:8][CH2:7][C@H:6]([C:9]([O:11]C)=[O:10])[CH2:5][CH2:4]1)#[N:2].[OH-].[Li+]>C1COCC1.O>[C:1]([C@H:3]1[CH2:4][CH2:5][C@H:6]([C:9]([OH:11])=[O:10])[CH2:7][CH2:8]1)#[N:2]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 178501117HCID 178501117, compound

Product 1

HCID 178511260HCID 178511260, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl trans-4-cyanocyclohexanecarboxylate (996 mg, 5.96 mmol) in THF (37 mL) was added a solution of 0.5 M lithium hydroxide in water (20 mL). The mixture was stirred overnight then the THF was removed in vacuo and the residual aqueous solution acidified to pH 4. The resulting mixture was extracted with ether (2×30 mL), EtOAc (2×30 mL) and CHCl3 (2×30 mL) then the combined extracts, dried over anhydrous sodium sulfate and concentrated in vacuo. This material was taken to the next step without any purification. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.43-1.73 (4H, m), 2.05-2.22 (4H, m) and 2.36-2.59 (2H, m).

Workup

  1. customthe THF was removed in vacuo
  2. extractionThe resulting mixture was extracted with ether (2×30 mL), EtOAc (2×30 mL) and CHCl3 (2×30 mL)
  3. dry with materialthe combined extracts, dried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThis material was taken to the next step without any purification

Sources & evidence

ORD record
ord-dcf1b28a238e4a269f02911e577f3857
Source dataset
uspto-grants-2010_04
Patent number
US07700594B2

Reaction notes

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