Sodium Hydroxide → 5-(((Benzyloxy)carbonyl)amino)bicyclo[3.2.1]octane-1-carboxylic acid

HRID 1408861Notes

Reaction equation

HRID 1408861 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C:12]12[CH2:19][C:16]([C:20]([O:22]C)=[O:21])([CH2:17][CH2:18]1)[CH2:15][CH2:14][CH2:13]2)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>CO>[CH2:1]([O:8][C:9]([NH:11][C:12]12[CH2:19][C:16]([C:20]([OH:22])=[O:21])([CH2:17][CH2:18]1)[CH2:15][CH2:14][CH2:13]2)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 68048076Methyl 5-(benzyloxycarbonylamino)bicyclo[3.2.1]octane-1-carboxylate

Product 1

HCID 679810565-(((Benzyloxy)carbonyl)amino)bicyclo[3.2.1]octane-1-carboxylic acidYield 49%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl 5-(benzyloxycarbonylamino)bicyclo-[3.2.1]octane-1-carboxylate (25 g, crude product) in methanol (200 mL) was added NaOH (5N, 50 mL) and the reaction mixture was refluxed for two hours. After cooled to room temperature, the mixture was concentrated under reduced pressure. The residue was diluted with water (100 mL) and extracted with diethyl ether (3×100 mL) to remove the organic impurities. The aqueous phase was adjusted to pH 1˜2 with 2N aq. HCl, and extracted with dichloromethane (3×100 mL). The combined organic layer was washed with brine, dried over sodium sulfate and concentrated under reduced pressure to afford 8.5 g (49%, steps 5 and 6) of 5-(benzyloxycarbonylamino)bicyclo[3.2.1]octane-1-carboxylic acid as a yellow oil. ESI-MS m/z: 304 (M+H)+.

Workup

  1. temperaturethe reaction mixture was refluxed for two hours
  2. concentrationthe mixture was concentrated under reduced pressure
  3. additionThe residue was diluted with water (100 mL)
  4. extractionextracted with diethyl ether (3×100 mL)
  5. customto remove the organic impurities
  6. extractionextracted with dichloromethane (3×100 mL)
  7. washThe combined organic layer was washed with brine
  8. dry with materialdried over sodium sulfate
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7fe8b980fe7040309dc10a5c9a6b8a0c
Source dataset
uspto-grants-2014_12
Patent number
US08921370B2

Reaction notes

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