Ethyl Acetate → 1-(4-Nitro-benzyl)-2-vinyl-pyrrolidine

HRID 2236515Notes

Reaction equation

HRID 2236515 reaction equation
C(O[C:6]([N:8]1[CH2:12][CH2:11][CH2:10][CH:9]1[CH:13]=[CH2:14])=O)(C)(C)C.[N+:15]([C:18]1[CH:25]=[CH:24][C:21](CBr)=[CH:20][CH:19]=1)([O-:17])=[O:16].C([O-])([O-])=O.[K+].[K+].CCOC(C)=O>C(Cl)Cl.C(O)(C(F)(F)F)=O.O>[N+:15]([C:18]1[CH:25]=[CH:24][C:21]([CH2:6][N:8]2[CH2:12][CH2:11][CH2:10][CH:9]2[CH:13]=[CH2:14])=[CH:20][CH:19]=1)([O-:17])=[O:16]

Participants

8

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 660114-Nitrobenzyl bromideHCID 139051562-Vinylpyrrolidine, N-BOC protected

Product 1

HCID 593001711-(4-Nitro-benzyl)-2-vinyl-pyrrolidineYield 85%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

2-Vinyl-pyrrolidine-1-carboxylic acid tert-butyl ester (300 mg, 1.52 mmol) is dissolved in CH2Cl2 (4 mL) to which TFA (0.55 mL) is added dropwisely. The resulting mixture is stirred until TLC showed no starting material. All the volatiles were removed under vacuum. CH3CN (5 mL) is added followed by 4-nitrobenzylbromide (400 mg, 1.85 mmol) and K2CO3 (1 g, 7.2 mmol). The mixture is stirred until TLC suggested no starting material left. EtOAc and H2O were added and the EtOAc layer is washed with brine and dried. After evaporating the EtOAc, the residue is purified with flash chromatography to provide the desired product (300 mg, 85%).

Workup

  1. additionis added dropwisely
  2. customAll the volatiles were removed under vacuum
  3. additionCH3CN (5 mL) is added
  4. stirringThe mixture is stirred until TLC
  5. waitleft
  6. washthe EtOAc layer is washed with brine
  7. customdried
  8. customAfter evaporating the EtOAc
  9. customthe residue is purified with flash chromatography

Sources & evidence

ORD record
ord-cd3ae3c3986b4e53b66d2616a7bf6558
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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