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

HRID 965919Notes

Reaction equation

HRID 965919 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-c3c48a34d1f74f49b72d2cdd5a756f3c
Source dataset
uspto-grants-2005_10
Patent number
US06951874B2

Reaction notes

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