Water → (2R,4R)-1-[(tert-butoxy)carbonyl]-4-methoxypyrrolidine-2-carboxylic acid

HRID 1796286Notes

Reaction equation

HRID 1796286 reaction equation
C[O:2][C:3]([C@H:5]1[CH2:9][C@@H:8]([O:10][CH3:11])[CH2:7][N:6]1[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])=[O:4].O.O[Li].O>C(#N)C>[C:15]([O:14][C:12]([N:6]1[CH2:7][C@H:8]([O:10][CH3:11])[CH2:9][C@@H:5]1[C:3]([OH:4])=[O:2])=[O:13])([CH3:18])([CH3:16])[CH3:17]

Participants

5

Reactant 3

HCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 541382851-(Tert-butyl) 2-methyl (2R,4R)-4-methoxypyrrolidine-1,2-dicarboxylate

Product 1

HCID 11459222(2R,4R)-1-[(tert-butoxy)carbonyl]-4-methoxypyrrolidine-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Into a solution of 5 (2.54 g, 9.80 mmol) in acetonitrile (20 mL) was added water (20 mL) and LiOH.H2O (1.64 g, 39.2 mmol). The mixture was stirred at RT for 28 h before removing the acetonitrile under reduced pressure. EtOAc was added to the residue that was then washed with 1N HCl. The aqueous layer was extracted with additional EtOAc and the combined organic layers were washed with brine and dried over MgSO4. The solution was concentrated under reduced pressure to reveal 6 (2.16 g, 90%) as a white solid. MS: APCI (AP−): 244.1 (M)−.

Workup

  1. custombefore removing the acetonitrile under reduced pressure
  2. additionEtOAc was added to the residue that
  3. washwas then washed with 1N HCl
  4. extractionThe aqueous layer was extracted with additional EtOAc
  5. washthe combined organic layers were washed with brine
  6. dry with materialdried over MgSO4
  7. concentrationThe solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-435dde5b3146427b96013b54cd377d97
Source dataset
uspto-grants-2006_04
Patent number
US07030141B2

Reaction notes

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