Sodium Hydroxide → (3R)-4-(3-(isobutoxycarbonylamino)pyrrolidine-1-carbonyloxy)adamantane-1-carboxylic acid

HRID 1948704Notes

Reaction equation

HRID 1948704 reaction equation
C([O:5][C:6]([NH:8][CH:9]1[CH2:13][CH2:12][N:11]([C:14]([O:16][CH:17]2[CH:24]3[CH2:25][C:20]4([C:27](=[O:29])N)[CH2:21][CH:22]([CH2:26][CH:18]2[CH2:19]4)[CH2:23]3)=[O:15])[CH2:10]1)=[O:7])(C)(C)C.[OH-:30].[Na+]>C1COCC1.CO>[CH2:17]([O:5][C:6]([NH:8][CH:9]1[CH2:13][CH2:12][N:11]([C:14]([O:16][CH:17]2[CH:24]3[CH2:25][C:20]4([C:27]([OH:30])=[O:29])[CH2:21][CH:22]([CH2:26][C@@H:18]2[CH2:19]4)[CH2:23]3)=[O:15])[CH2:10]1)=[O:7])[CH:18]([CH3:26])[CH3:19]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 75968129(1-Carbamoyl-4-adamantyl) 3-(tert-butoxycarbonylamino)pyrrolidine-1-carboxylate

Product 1

HCID 66884403(3R)-4-(3-(isobutoxycarbonylamino)pyrrolidine-1-carbonyloxy)adamantane-1-carboxylic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of (3R) (1-(methoxycarbonyl)-4-adamantyl) 3-(isobutoxycarbonylamino)pyrrolidine-1-carboxylate (130 mg, 0.28 mmol) in THF (5 mL) and MeOH (10 mL) was added 5% aq NaOH (5 mL). The mixture was stirred at rt for 3 d. The mixture was concentrated under reduced pressure, diluted with water (15 mL) and washed with ether (80 mL). The aqueous layer was diluted with 10% aq citric acid (30 mL) and extracted with EtOAc (3×40 mL). The combined organic extracts were dried over MgSO4 and concentrated to leave (3R)-4-(3-(isobutoxycarbonylamino)pyrrolidine-1-carbonyloxy)adamantane-1-carboxylic acid (178 mg) as an oil.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. additiondiluted with water (15 mL)
  3. washwashed with ether (80 mL)
  4. additionThe aqueous layer was diluted with 10% aq citric acid (30 mL)
  5. extractionextracted with EtOAc (3×40 mL)
  6. dry with materialThe combined organic extracts were dried over MgSO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-4be9c03cdddb473498828a584328c8c3
Source dataset
uspto-grants-2013_03
Patent number
US08399504B2

Reaction notes

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