Hydrochloric Acid → Tert-butyl 3-oxopyrrolidine-1-carboxylate

HRID 880711Notes

Reaction equation

HRID 880711 reaction equation
Cl.[C:2]([N:9]1[CH2:13][CH2:12][CH:11]([OH:14])[CH2:10]1)([O:4][C:5]([CH3:8])([CH3:7])[CH3:6])=[O:3]>CS(C)=O.C(N(CC)CC)C>[C:5]([O:4][C:2]([N:9]1[CH2:13][CH2:12][C:11](=[O:14])[CH2:10]1)=[O:3])([CH3:8])([CH3:6])[CH3:7]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 44169391-Boc-3-pyrrolidinol

Product 1

HCID 471360Tert-butyl 3-oxopyrrolidine-1-carboxylateYield 58%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 8471TriethylamineSolvent

Procedure

In a 1 l three-necked flask, 10 g of N-Boc-3-hydroxypyrrolidine are dissolved in 350 ml of dimethyl sulphoxide in the presence of 52.3 ml of triethylamine. 28 g of pyridine-sulphur trioxide complex dissolved in 350 ml of dimethyl sulphoxide are added dropwise to the above solution. The reaction mixture is stirred for 4 hours at ambient temperature. The reaction medium is acidified to pH 4.5-5 with a 1M solution of hydrochloric acid and the reaction mixture is then extracted with ethyl acetate. The organic phases are combined and then dried over anhydrous sodium sulphate. The residue is filtered through silica gel (1/1 heptane/ethyl acetate). 5.7 g of 3-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester are obtained. Yield: 58%.

Workup

  1. additionare added dropwise to the above solution
  2. extractionthe reaction mixture is then extracted with ethyl acetate
  3. dry with materialdried over anhydrous sodium sulphate
  4. filtrationThe residue is filtered through silica gel (1/1 heptane/ethyl acetate)

Sources & evidence

ORD record
ord-137c4723246f42ff95ba60a6116fb0dc
Source dataset
uspto-grants-2015_03
Patent number
US08993596B2

Reaction notes

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