Benzyl Chloride → HCID 22601252, compound

HRID 2308212Notes

Reaction equation

HRID 2308212 reaction equation
[C:1]([N:3]1[CH2:7][CH2:6][CH:5]([OH:8])[CH2:4]1)#[N:2].[H-].[Na+].[CH2:11](Cl)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[NH4+].[Cl-]>CN(C=O)C.CO>[CH2:11]([O:8][CH:5]1[CH2:6][CH2:7][N:3]([C:1]#[N:2])[CH2:4]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[CH2:11]([O:8][CH2:5][C:6]1[CH:7]=[CH:7][CH:6]=[CH:5][CH:4]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

7

Reactant 4

HCID 7503Benzyl ChlorideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 9964077HCID 9964077, compound

Product 1

HCID 22601252HCID 22601252, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

Following general procedure 12, to a cold (0° C.), stirred solution of the alcohol (23) (58 mg, 1 equiv.) in DMF (5 mL) was added NaH (60% in oil, 31 mg, 1.5 equiv.). The suspension was stirred at 0° C. for 40 minutes followed by the addition of the benzyl chloride (120 uL, 2 equiv.). The suspension was warmed to rt and stirred for 6 h. MeOH was added followed by sat. aq. NH4Cl. The aqueous phase was extracted with EtOAc (3×) and the combined organic extracts were washed with brine, dried (MgSO4) and concentrated under reduced pressure. The residue was purified by flash chromatography (25% EtOAc in hexane) to afford the desired benzyl ether 3-(benzyloxy)-1-cyanopyrrolidine (24).

Workup

  1. temperatureThe suspension was warmed to rt
  2. stirringstirred for 6 h
  3. extractionThe aqueous phase was extracted with EtOAc (3×)
  4. washthe combined organic extracts were washed with brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by flash chromatography (25% EtOAc in hexane)

Sources & evidence

ORD record
ord-7d38e8db171e4b9e9063148f5d12e46d
Source dataset
uspto-grants-2004_12
Patent number
US06835727B2

Reaction notes

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