Lithium hydroxide, monohydrate → cis-2-((tert-Butoxycarbonyl)amino)cyclohexanecarboxylic acid

HRID 1593985Notes

Reaction equation

HRID 1593985 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:14][CH2:13][CH2:12][CH2:11][C@H:10]1[C:15]([O:17]CC)=[O:16])=[O:7])([CH3:4])([CH3:3])[CH3:2].O.[OH-].[Li+]>CO.O>[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:14][CH2:13][CH2:12][CH2:11][C@H:10]1[C:15]([OH:17])=[O:16])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 56595230(1R,2S)-Ethyl 2-((tert-butoxycarbonyl)amino)cyclohexanecarboxylate

Product 1

HCID 1512487cis-2-((tert-Butoxycarbonyl)amino)cyclohexanecarboxylic acidYield 93.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To 6.05 grams (22.3 mmol) of the ester of step 1 dissolved in 25 mL methanol was added 2.6 g (55.74 mmol) lithium hydroxide monohydrate dissolved in 10 mL water. The mixture was stirred for 48 hours, partitioned between ethyl acetate and 1 N HCl, dried over magnesium sulfate and concentrated to obtain 5.05 g of the crude (1R,2S)-2-[(tert-butoxycarbonyl)amino]cyclohexanecarboxylic acid.

Workup

  1. custompartitioned between ethyl acetate and 1 N HCl
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-1a60637ecfbe41458c8e9c79125c24cf
Source dataset
uspto-grants-2007_11
Patent number
US07300934B2

Reaction notes

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