Morpholine → (E)-tert-butyl 4-morpholino-2-butenoate

HRID 2284649Notes

Reaction equation

HRID 2284649 reaction equation
[C:1]([O:5][C:6](=[O:11])/[CH:7]=[CH:8]/[CH2:9]I)([CH3:4])([CH3:3])[CH3:2].[NH:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1.C(=O)([O-])O.[Na+].C(OCC)(=O)C>O1CCCC1>[O:15]1[CH2:16][CH2:17][N:12]([CH2:9]/[CH:8]=[CH:7]/[C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:11])[CH2:13][CH2:14]1

Participants

6

Reactant 4

HCID 8083MorpholineHCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 900517224-Iodocrotonic acid tert-butyl ester

Product 1

HCID 90051723(E)-tert-butyl 4-morpholino-2-butenoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-iodocrotonic acid tert-butyl ester (310 mg) synthesized according to the method described in Journal of Medicinal Chemistry, 2005, vol. 48, pp. 1107-1131 in tetrahydrofuran (3 mL), morpholine (200 μL) was added under ice cooling, and the mixture was stirred at room temperature for 13 hours. To the reaction mixture, saturated aqueous sodium hydrogencarbonate and ethyl acetate were added. The organic layer was separated, washed successively with water and saturated aqueous sodium chloride, and then dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to obtain (E)-tert-butyl 4-morpholino-2-butenoate (B14, 180 mg).

Workup

  1. customThe organic layer was separated
  2. washwashed successively with water and saturated aqueous sodium chloride
  3. dry with materialdried over anhydrous sodium sulfate
  4. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-657286f0b5f34f2e87bcf03f80570869
Source dataset
uspto-grants-2015_09
Patent number
US09145415B2

Reaction notes

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