4-Methylmorpholine → O-Benzylhydroxylamine

HRID 727564Notes

Reaction equation

HRID 727564 reaction equation
C1N=CN(C(N2C=NC=C2)=O)C=1.CC1C=CC(S(NCCC(C2(CC(C)C)CCN(CCC3C=CC=CC=3)C2=O)C(O)=O)(=O)=O)=CC=1.Cl.[CH2:49]([O:56][NH2:57])[C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1.CN1CCOCC1>CCOC(C)=O.C(Cl)Cl>[CH2:49]([O:56][NH2:57])[C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1

Participants

7

Reactant 4

HCID 79724-MethylmorpholineHCID 682631,1'-CarbonyldiimidazoleHCID 102312Benzyloxyamine hydrochlorideHCID 19705459HCID 19705459, compound

Product 1

HCID 102313O-Benzylhydroxylamine

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

CDI (162 mg) is added to a solution of α-[2-[[(4-methylphenyl)sulfonyl]amino]ethyl]-3-(2-methylpropyl)-2-oxo-1-(2-phenylethyl)-3-pyrrolidineacetic acid (453 mg) and CH2Cl2 (5.0 mL). The solution is stirred for 1 hour at room temperature and then O-benzylhydroxylamine hydrochloride (192 mg) and 4-methylmorpholine (0.13 mL) are added. The solution is stirred for 16 h at room temperature. The solution is diluted with 60 mL of EtOAc which is washed with 10% HCl, brine, dried (MgSO4), filtered, and concentrated. Purification by flash chromatography (1:1 hexane:EtOAc) provides a lactam intermediate with no evidence of O-benzylhydroxylamine incorporation:

Workup

  1. stirringThe solution is stirred for 16 h at room temperature
  2. washis washed with 10% HCl, brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by flash chromatography (1:1 hexane:EtOAc)

Sources & evidence

ORD record
ord-b8dfe9019783445e962fac852c4206de
Source dataset
uspto-grants-1998_01
Patent number
US05712300

Reaction notes

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