Sodium Hydroxide → HCID 178484813, compound

HRID 1671756Notes

Reaction equation

HRID 1671756 reaction equation
[CH3:1][NH:2][C@@H:3]1[CH2:8][CH2:7][C@H:6]([C:9]([O:11]C)=[O:10])[CH2:5][CH2:4]1.[OH-].[Na+]>C1COCC1.O>[CH3:1][NH:2][C@@H:3]1[CH2:8][CH2:7][C@H:6]([C:9]([OH:11])=[O:10])[CH2:5][CH2:4]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 178484818HCID 178484818, compound

Product 1

HCID 178484813HCID 178484813, compoundYield 91.4%

Reagents, catalysts & solvents 1

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

Conditions

Temperature
0 °C

Procedure

The methyl cis-4-(methylamino)cyclohexanecarboxylate (3 g, 0.0175 mol) from above was dissolved in a THF/H2O (10 mL) mixture and was cooled to 0° C. Next 2 L of a 0.025 M solution of NaOH was added slowly. The mixture was stirred a 0° C. for another 0.5 hour. The mixture was then acidified to pH 7-8 and extracted with ethyl acetate. The water layer was acidified to pH 3-4 and extracted with ethyl acetate. The organic layer was dried over Na2SO4 and concentrated to give 2.49 g (0.016 mol, 90% yield) of product.

Workup

  1. extractionextracted with ethyl acetate
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-2ee4970b27494b39b47cbfef0fdddcbc
Source dataset
uspto-grants-2011_08
Patent number
US07994317B2

Reaction notes

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