Sodium Hydroxide → 4-(((Tert-butoxy)carbonyl)amino)bicyclo(2.2.1)heptane-1-carboxylic acid

HRID 2204485Notes

Reaction equation

HRID 2204485 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]12[CH2:15][C:12]([C:16]([O:18]C)=[O:17])([CH2:13][CH2:14]1)[CH2:11][CH2:10]2)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>C1COCC1.CO>[C:1]([O:5][C:6]([NH:8][C:9]12[CH2:15][C:12]([C:16]([OH:18])=[O:17])([CH2:11][CH2:10]1)[CH2:13][CH2:14]2)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 58009867Methyl 4-{[(tert-butoxy)carbonyl]amino}bicyclo[2.2.1]heptane-1-carboxylate

Product 1

HCID 580099444-(((Tert-butoxy)carbonyl)amino)bicyclo(2.2.1)heptane-1-carboxylic acidYield 81%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 4-(tert-butoxycarbonylamino)bicyclo[2.2.1]heptane-1-carboxylate (2.21 g, 8.20 mmol) in THF (27 mL) and MeOH (14 mL) was added aqueous NaOH (1 N, 20.0 mL, 20.0 mmol). The mixture was stirred at room temperature for about 16 h and concentrated to dryness under reduced pressure. Water (25 mL) was added to the remaining residue and the mixture was extracted with Et2O (2×25 mL) and the Et2O extracts were discarded. The aqueous layer was acidified to about pH 4 using aqueous 6 N HCl and extracted with Et2O (3×10 mL). The combined organic layers were dried over anhydrous MgSO4, filtered, and concentrated to dryness under reduced pressure to provide 4-(tert-butoxycarbonylamino)bicyclo[2.2.1]heptane-1-carboxylic acid as an off-white solid (1.69 g, 81%): 1H NMR (400 MHz, DMSO-d6) δ 12.07 (s, 1H), 7.00 (s, 1H), 2.00-1.69 (m, 6H), 1.67-1.45 (m, 4H), 1.37 (s, 9H).

Workup

  1. concentrationconcentrated to dryness under reduced pressure
  2. additionWater (25 mL) was added to the remaining residue
  3. extractionthe mixture was extracted with Et2O (2×25 mL)
  4. extractionextracted with Et2O (3×10 mL)
  5. dry with materialThe combined organic layers were dried over anhydrous MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-a0a9d7d50bca464396c207478c79df79
Source dataset
uspto-grants-2016_06
Patent number
US09365579B2

Reaction notes

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