Pyridine → 1-Pyrrolidinecarboxylic acid, 2-oxo-, 1,1-dimethylethyl ester

HRID 496217Notes

Reaction equation

HRID 496217 reaction equation
N1C=CC=CC=1.[C:7]([O:11][C:12]([N:14]1[CH2:18][CH2:17][CH:16](O)[CH2:15]1)=[O:13])([CH3:10])([CH3:9])[CH3:8].C(OC(=O)C)(=[O:22])C.C(OCC)(=O)C>C(Cl)Cl.[O-2].[Cr+6].[O-2].[O-2]>[C:7]([O:11][C:12]([N:14]1[CH2:18][CH2:17][CH2:16][C:15]1=[O:22])=[O:13])([CH3:10])([CH3:9])[CH3:8]

Participants

7

Reactant 4

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 8857Ethyl AcetateHCID 44169391-Boc-3-pyrrolidinol

Product 1

HCID 3790001-Pyrrolidinecarboxylic acid, 2-oxo-, 1,1-dimethylethyl ester

Reagents, catalysts & solvents 2

HCID 10219390chromium (VI) trioxideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

Chromium (vi) oxide (800 mg, 8.0 mmol) was added to pyridine (1.6 mL) in CH2Cl2 (10 mL) and the resulting solution was stirred for 15 min at room temperature. A solution of tert.butyl-3-hydroxy-1-pyrrolidinecarboxylate (374.5 mg, 2.0 mmol) in CH2Cl2 (5 mL) was added, immediately followed by acetic anhydride and the reaction mixture kept at room temperature for 15 min. After addition of ethyl acetate, decanted and filtered through a short column of silica gel. The filtrate was concentrated to give the subtitled product (193 mg) and was used directly in the next step.

Workup

  1. waitthe reaction mixture kept at room temperature for 15 min
  2. customdecanted
  3. filtrationfiltered through a short column of silica gel
  4. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-04b00615885c44be95f61be3700d11ae
Source dataset
uspto-grants-2005_09
Patent number
US06943188B2

Reaction notes

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