Ethyl Acetate → HCID 66733609, compound

HRID 2047004Notes

Reaction equation

HRID 2047004 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH:13]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:12][CH2:11][CH:10]([C:21](O)=[O:22])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Li].C[Si](N[Si](C)(C)C)(C)C.[C:34]([O:37][CH2:38][CH3:39])(=[O:36])[CH3:35]>C1COCC1>[CH2:38]([O:37][C:34](=[O:36])[CH2:35][C:21]([CH:10]1[CH2:9][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH:13]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:12][CH2:11]1)=[O:22])[CH3:39]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 57426343Lithium bis(trimethylsilyl)amideHCID 67494799HCID 67494799, compound

Product 1

HCID 66733609HCID 66733609, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

1,6-bis(tert-butoxycarbonyl)piperidine-3-carboxylic acid (41.4 mmol, 13.6 g) and N,N′-carbonyldiimidazole (CDI) (51.75 mmol, 8.4 g) in anhydrous THF (140 mL) were stirred 16 h at room temperature under argon. In a separate, sealed and argon-flushed flask, lithium HMDS (1.0 M in THF, 86.9 mmol) is added to 80 mL anhydrous THF stirring at −78° C. To this solution is added dropwise anhydrous ethyl acetate (89 mmol, 8.69 mL). This solution is allowed to stir at −78° C. for 1 hour prior to the dropwise addition of the original CDI/acid solution that had been stirred overnight. The reaction mixture is allowed to stir and warm to room temperature overnight. The reaction is then quenched with saturated NH4Cl(aq) (250 mL) and extracted with Et2O (100×2). The combined organics are then washed with water, saturated brine, and dried over Na2SO4. The solvent is removed in vacuo and the residue (12.6 g) was used in the next step without further purification.

Workup

  1. customIn a separate, sealed
  2. customargon-flushed flask
  3. stirringhad been stirred overnight
  4. stirringto stir
  5. temperaturewarm to room temperature overnight
  6. customThe reaction is then quenched with saturated NH4Cl(aq) (250 mL)
  7. extractionextracted with Et2O (100×2)
  8. washThe combined organics are then washed with water, saturated brine
  9. dry with materialdried over Na2SO4
  10. customThe solvent is removed in vacuo
  11. customthe residue (12.6 g) was used in the next step without further purification

Sources & evidence

ORD record
ord-d5914694285c42549f77232723c1c805
Source dataset
uspto-grants-2013_11
Patent number
US08591943B2

Reaction notes

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