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

HRID 737072Notes

Reaction equation

HRID 737072 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 pH12-14 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-977be4290a0a44aca8e30df0fc32e7be
Source dataset
uspto-grants-2009_09
Patent number
US07595397B2

Reaction notes

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