Lithium hydroxide, monohydrate → (Rac)-1-[5-(biphenyl-4-yloxymethyl)-furan-2-carbonyl]-piperidine-2-carboxylic acid

HRID 899541Notes

Reaction equation

HRID 899541 reaction equation
O.[OH-].[Li+].C([O:6][C:7]([CH:9]1[CH2:14][CH2:13][CH2:12][CH2:11][N:10]1[C:15]([C:17]1[O:18][C:19]([CH2:22][O:23][C:24]2[CH:29]=[CH:28][C:27]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[CH:26][CH:25]=2)=[CH:20][CH:21]=1)=[O:16])=[O:8])C>O.O1CCCC1.CO>[C:27]1([C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH:26]=[CH:25][C:24]([O:23][CH2:22][C:19]2[O:18][C:17]([C:15]([N:10]3[CH2:11][CH2:12][CH2:13][CH2:14][CH:9]3[C:7]([OH:8])=[O:6])=[O:16])=[CH:21][CH:20]=2)=[CH:29][CH:28]=1

Participants

6

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 59694988(Rac)-1-[5-(biphenyl-4-yloxymethyl)-furan-2-carbonyl]-piperidine-2-carboxylic acid ethyl ester

Product 1

HCID 59694985(Rac)-1-[5-(biphenyl-4-yloxymethyl)-furan-2-carbonyl]-piperidine-2-carboxylic acidYield 83%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of lithium hydroxide monohydrate (0.027 g, 0.64 mmol) in water (1 mL) was added to a solution of (rac)-1-[5-(biphenyl-4-yloxymethyl)-furan-2-carbonyl]-piperidine-2-carboxylic acid ethyl ester (0.085 g, 0.2 mmol) in tetrahydrofuran (3 mL) and methanol (1 mL). The mixture was stirred overnight at room temperature and then the solvents were evaporated under reduced pressure. Water and ethyl acetate were added, and the mixture was acidified to pH 2 with 1 M HCl and the mixture was extracted three times with ethyl acetate. The combined organic layers were dried (sodium sulfate), filtered, and evaporated. The residue was triturated with ether. The ether and dissolved impurities were removed by Pasteur pipette to give (rac)-1-[5-(biphenyl-4-yloxymethyl)-furan-2-carbonyl]-piperidine-2-carboxylic acid (66 mg, 83%) as a white solid.

Workup

  1. customthe solvents were evaporated under reduced pressure
  2. additionWater and ethyl acetate were added
  3. extractionthe mixture was extracted three times with ethyl acetate
  4. dry with materialThe combined organic layers were dried (sodium sulfate)
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was triturated with ether
  8. dissolutionThe ether and dissolved impurities
  9. customwere removed by Pasteur pipette

Sources & evidence

ORD record
ord-c77c35db5a194ed982826e4aa09d9a01
Source dataset
uspto-grants-2008_04
Patent number
US07355049B2

Reaction notes

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