Lithium Hydroxide → 2-(1-((((Tert-butoxy)carbonyl)amino)methyl)cyclohexyl)acetic acid

HRID 1713028Notes

Reaction equation

HRID 1713028 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:12](=[O:13])[CH2:11][C:10]2([CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Li+].[OH-].CCCCCC.BrC1C=CC=C([OH:34])C=1C>C1COCC1.C(OCC)(=O)C>[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1([CH2:11][C:12]([OH:34])=[O:13])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 3939Lithium HydroxideHCID 8058HexaneHCID 111714303-Bromo-2-methylphenolHCID 685035643-Oxo-2-aza-spiro[4.5]decane-2-carboxylic acid tert-butyl ester

Product 1

HCID 27559412-(1-((((Tert-butoxy)carbonyl)amino)methyl)cyclohexyl)acetic acidYield 84%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
25 °C

Procedure

3-oxo-2-aza-spiro[4.5]decane-2-carboxylic acid tert-butyl ester (253 mg, 1 mmol) was dissolved in THF (5 ml) and an aqueous solution of 1N LiOH (72 mg/3 ml, 3 molequivalents) was added thereto. The mixture was stirred at 25° C. for 6 hours while monitoring the progress of the reaction by TLC, using a 6:4 hexane:ethyl acetate mixture as eluent and bromocresol for developing the TLC plate. Reaction completion was indicated by the appearance of a more polar spot while the starting material gradually disappeared from the middle of the TLC plate. Thereafter, the THF was evaporated under reduced pressure and the basic aqueous residue was acidified by the addition of 15 drops of concentrated HCl (pH 3) and extracted with ethyl acetate. The aqueous layer was washed with ethyl acetate and the combined organic layer was washed with water, dried over NaSO4 and evaporated under reduced pressure to give [1-(tert-butoxycarbonylamino-methyl)-cyclohexyl]-acetic acid (228 mg, 84% yield) as a colorless solid.

Workup

  1. customthe progress of the reaction by TLC
  2. customReaction completion
  3. customThereafter, the THF was evaporated under reduced pressure
  4. additionthe basic aqueous residue was acidified by the addition of 15 drops of concentrated HCl (pH 3)
  5. extractionextracted with ethyl acetate
  6. washThe aqueous layer was washed with ethyl acetate
  7. washthe combined organic layer was washed with water
  8. dry with materialdried over NaSO4
  9. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-8fc533666e9f439aa5cef23bfb2e4ef4
Source dataset
uspto-grants-2010_09
Patent number
US07795255B2

Reaction notes

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