(Diethylamino)sulfur trifluoride → Tert-butyl 3-cyano-3-(fluoromethyl)azetidine-1-carboxylate

HRID 217428

Reaction equation

HRID 217428 reaction equation
[C:1]([C:3]1([CH2:14]O)[CH2:6][N:5]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:4]1)#[N:2].CCN(S(F)(F)[F:22])CC.C([O-])(O)=O.[Na+]>C(Cl)Cl>[C:1]([C:3]1([CH2:14][F:22])[CH2:6][N:5]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:4]1)#[N:2]

Participants

5

Reactant 3

HCID 123472(Diethylamino)sulfur trifluorideHCID 516892Sodium BicarbonateHCID 584389531,1-Dimethylethyl 3-cyano-3-(hydroxymethyl)-1-azetidinecarboxylate

Product 1

HCID 58293513Tert-butyl 3-cyano-3-(fluoromethyl)azetidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

tert-Butyl 3-cyano-3-(hydroxymethyl)azetidine-1-carboxylate (5.0 g) was dissolved in DCM (100 mL). At 0° C., DAST (3.74 mL) was added thereto, followed by stirring at 0° C. for 3 hours. Three hours later, to the reaction liquid was added an aqueous NaHCO3 solution (100 mL), followed by extraction with DCM (50 mL) three times. The organic layer was washed with brine, dried over MgSO4, and then concentrated. The residue was purified by silica gel column chromatography (automatic purification device, hexane:EtOAc=100:0 to 50:50) to obtain tert-butyl 3-cyano-3-(fluoromethyl)azetidine-1-carboxylate (1.24 g) as a brown solid.

Workup

  1. customThree hours later, to the reaction liquid
  2. extractionfollowed by extraction with DCM (50 mL) three times
  3. washThe organic layer was washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography (automatic purification device, hexane:EtOAc=100:0 to 50:50)

Sources & evidence

ORD record
ord-3a948117613649c2a92702f858a50e0a
Source dataset
uspto-grants-2012_06
Patent number
US08193378B2

Linked notes

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