Sodium hydride → (S)-5-benzyloxymethyl-2,2-diphenylmorpholine-4-carboxylic acid tert-butyl ester

HRID 20395Notes

Reaction equation

HRID 20395 reaction equation
[C:1]([O:5][C:6](=[O:35])[NH:7][C@@H:8]([CH2:26][O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[CH2:9][O:10][C:11]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH2:12]I)([CH3:4])([CH3:3])[CH3:2].[H-].[Na+]>CN(C)C=O.C(OCC)(=O)C>[C:1]([O:5][C:6]([N:7]1[C@@H:8]([CH2:26][O:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH2:9][O:10][C:11]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:12]1)=[O:35])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 24758Sodium hydrideHCID 68558007[(S)-1-benzyloxymethyl-2-(2-iodo-1,1-diphenylethoxy)-ethyl]-carbamic acid tert-butyl ester

Product 1

HCID 68561079(S)-5-benzyloxymethyl-2,2-diphenylmorpholine-4-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To [(S)-1-benzyloxymethyl-2-(2-iodo-1,1-diphenylethoxy)-ethyl]-carbamic acid tert-butyl ester (4.74 g, 8.07 mmol) in N,N-dimethylformamide (70 mL) at room temperature add sodium hydride (0.452 g, 11.3 mmol, 60% dispersion in mineral oil). Heat reaction mixture to 60° C. for 4 hours, cool to room temperature and dilute with ethyl acetate (˜400 mL). Wash with water and saturated aqueous sodium chloride, dry (magnesium sulfate), filter and concentrate. Purify on silica gel eluting with 0:100 to 20:80 ethyl acetate:hexanes to give the desired compound as an oil.

Workup

  1. temperatureHeat
  2. customreaction mixture to 60° C. for 4 hours
  3. washWash with water and saturated aqueous sodium chloride
  4. dry with materialdry (magnesium sulfate)
  5. filtrationfilter
  6. concentrationconcentrate
  7. customPurify on silica gel eluting with 0:100 to 20:80 ethyl acetate

Sources & evidence

ORD record
ord-233069d86f814897b3e3d35b35bd405f
Source dataset
uspto-grants-2010_06
Patent number
US07745438B2

Reaction notes

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