Sodium hydride → Ethyl 3-(1-Boc-2-pyrrolidinyl)acrylate

HRID 910792Notes

Reaction equation

HRID 910792 reaction equation
[H-].[Na+].[C:3]([O:7][C:8]([N:10]1[CH2:14][CH2:13][CH2:12][CH:11]1[CH:15]=O)=[O:9])([CH3:6])([CH3:5])[CH3:4].CCCCCC.[CH3:23][CH2:24][O:25][C:26]([CH3:28])=[O:27]>C1COCC1.CCOC(C)=O.[Cl-].[Na+].O>[C:3]([O:7][C:8]([N:10]1[CH2:14][CH2:13][CH2:12][CH:11]1[CH:15]=[CH:28][C:26]([O:25][CH2:24][CH3:23])=[O:27])=[O:9])([CH3:4])([CH3:5])[CH3:6]

Participants

7

Reactant 3

HCID 24758Sodium hydrideHCID 42278151-Boc-2-FormylpyrrolidineHCID 21226206Ethyl acetate hexane

Product 1

HCID 53933727Ethyl 3-(1-Boc-2-pyrrolidinyl)acrylate

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A 2 L, 3-necked round bottomed flask equipped with an overhead stirred and nitrogen inlet was charged with NaH (60%, 10.0 g, 0.25 mol) and anhydrous THF (200 mL). To the stirred mixture was slowly added triethylphosphonoacetate (53.8 g, 0.24 mol) over 20 minutes. A solution of crude 2-formyl-pyrrolidine-1-carboxylic acid tert-butyl ester (40 g, 0.20 mol) in THF (75 mL) was added dropwise. The solution turned orange and the stirring was continued for 1 h until no aldehyde remained by TLC analysis [1:1 hexane/EtOAc, Rf(aldehyde)=0.6; Rf(14)=0.8]. The solution was diluted with EtOAc and brine and the layers were separated. The EtOAc layer was washed with 1M HCl, brine, dried over anhydrous Na2SO4, filtered, and concentrated to afford 14 (67 g) as a yellow oil which was used without further purification. 1H NMR (CDCl3, 300 MHz) δ6.92-6.76 (m, 1H), 5.82 (d, 1H), 4.56-4.32 (m, 1H), 4.25-4.12 (m, 2H), 3.48-3.27 (m, 2H), 2.20-1.98 (m, 1H), 1.91-1.72 (m, 2H), 1.43 (s, 9H), 1.25 (t, 3H) ppm.

Workup

  1. customA 2 L, 3-necked round bottomed flask equipped with an overhead
  2. customover 20 minutes
  3. customthe layers were separated
  4. washThe EtOAc layer was washed with 1M HCl, brine
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-4cf57688bc8d4db5a84b440736e72b08
Source dataset
uspto-grants-2011_09
Patent number
US08022230B2

Reaction notes

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