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

HRID 72133Notes

Reaction equation

HRID 72133 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-82e8306bf39a466bb1d0753033794bd7
Source dataset
uspto-grants-2014_09
Patent number
US08828985B2

Reaction notes

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