HCID 57849580, compound → (2S)-2-Phenylmorpholine

HRID 2076800Notes

Reaction equation

HRID 2076800 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][O:11][C@@H:10]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:9]1)=O)(C)(C)C>Cl.O1CCOCC1>[C:14]1([C@@H:10]2[O:11][CH2:12][CH2:13][NH:8][CH2:9]2)[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

4

Reactant 1

HCID 57849580HCID 57849580, compound

Product 1

HCID 937783(2S)-2-PhenylmorpholineYield 77.8%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

1.280 g (S)-2-Phenyl-morpholine-4-carboxylic acid tert-butyl ester was dissolved in 31 mL 4N HCl in dioxane and stirred at room temperature overnight. Concentrated in vacuo and diluted with 1N HCl. The aqueous was extracted with ether and then basicified to pH 12-14 with 2N NaOH followed by extraction with DCM. The organic layers were dried over Na2SO4, filtered and concentrated in vacuo to afford 617 mg of product by H NMR. 78% yield.

Workup

  1. concentrationConcentrated in vacuo
  2. additiondiluted with 1N HCl
  3. extractionThe aqueous was extracted with ether
  4. extractionfollowed by extraction with DCM
  5. dry with materialThe organic layers were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-bb26e92263f941a8ac5abc575829733c
Source dataset
uspto-grants-2011_04
Patent number
US07928103B2

Reaction notes

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