Water → 2-Benzyl 4-(tert-butyl) morpholine-2,4-dicarboxylate

HRID 42239Notes

Reaction equation

HRID 42239 reaction equation
[CH3:1][C:2]([O:5][C:6]([N:8]1[CH2:13][CH2:12][O:11][CH:10]([C:14]([OH:16])=[O:15])[CH2:9]1)=[O:7])([CH3:4])[CH3:3].C(=O)([O-])[O-].[K+].[K+].Br[CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.O>CN(C)C=O.ClCCl>[N:8]1([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:13][CH2:12][O:11][CH:10]([C:14]([O:16][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[O:15])[CH2:9]1

Participants

7

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 27559654-((Tert-butoxy)carbonyl)morpholine-2-carboxylic acid

Product 1

HCID 583678282-Benzyl 4-(tert-butyl) morpholine-2,4-dicarboxylateYield 85.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
20 °C

Procedure

4-{[(1,1-Dimethylethyl)oxy]carbonyl}-2-morpholinecarboxylic acid [Supplied by NeoMPS] (1 g, 4.32 mmol) was dissolved in N,N-dimethylformamide (20 ml) and potassium carbonate (0.598 g, 4.32 mmol) added. The mixture was stirred under nitrogen for 15 minutes at 20° C. Bromomethylbenzene (0.514 ml, 4.32 mmol) was added and the mixture stirred under nitrogen at room temperature for 18 hr. Water (25 ml) and dichloromethane (20 ml) were added and separated by hydrophobic fit. The aqueous phase was extracted with dichloromethane (2×20 ml). The organic phases were combined and the solvent was removed in vacuo. To the residue 1% lithium chloride solution (20 ml) and diethyl ether (20 ml) were added. The phases were separated and the aqueous phase was extracted with diethyl ether (2×15 ml). The combined organic phases were dried over magnesium sulphate and the solvent was removed in vacuo to give the title compound (1.19 g) as a colourless oil.

Workup

  1. stirringthe mixture stirred under nitrogen at room temperature for 18 hr
  2. customseparated by hydrophobic fit
  3. extractionThe aqueous phase was extracted with dichloromethane (2×20 ml)
  4. customthe solvent was removed in vacuo
  5. additionTo the residue 1% lithium chloride solution (20 ml) and diethyl ether (20 ml) were added
  6. customThe phases were separated
  7. extractionthe aqueous phase was extracted with diethyl ether (2×15 ml)
  8. dry with materialThe combined organic phases were dried over magnesium sulphate
  9. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-dd4c7873eef34afaa97cb35018e96b1c
Source dataset
uspto-grants-2013_09
Patent number
US08536169B2

Reaction notes

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