Acetonitrile → HCID 53917917, compound

HRID 1276356Notes

Reaction equation

HRID 1276356 reaction equation
[C:1]([O:5][C:6]([NH:8][N:9]1[CH2:13][CH2:12][C@H:11](OS(C)(=O)=O)[CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([O-])(O)=O.[Na+].[C:24](#[N:26])C>[C-]#N.C([N+](CCCC)(CCCC)CCCC)CCC>[C:1]([O:5][C:6]([NH:8][N:9]1[CH2:13][CH2:12][C@H:11]([C:24]#[N:26])[CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 516892Sodium BicarbonateHCID 54252157HCID 54252157, compound

Product 1

HCID 53917917HCID 53917917, compound

Reagents, catalysts & solvents 1

HCID 165872Tetrabutylammonium CyanideCatalyst

Conditions

Temperature
65 °C

Procedure

(S)-1-(tert-Butoxycarbonylamino)-3-methanesulfonyloxypyrrolidine (39 g, 0.15 mol) was dissolved in acetonitrile (250 mL) and tetra-n-butylammonium cyanide (75 g, 0.28 mol, 1.9 equiv.) was added. The resulting mixture was heated at 65° C. for 6 h and then cooled to room temperature. Saturated NaHCO3 (500 mL) was added and the reaction mixture extracted with toluene (750 mL and 300 mL). The combined organic layers were washed with water and concentrated under reduced pressure to give a brown oil. This crude material was purified by flash chromatography with 20% ethyl acetate in hexane to give (S)-1-(tert-butoxycarbonylamino)-3-cyanopyrrolidine as a yellow oil (13.5 g).

Workup

  1. temperaturecooled to room temperature
  2. extractionthe reaction mixture extracted with toluene (750 mL and 300 mL)
  3. washThe combined organic layers were washed with water
  4. concentrationconcentrated under reduced pressure
  5. customto give a brown oil
  6. customThis crude material was purified by flash chromatography with 20% ethyl acetate in hexane

Sources & evidence

ORD record
ord-1c021f641fa3417285a81fc55c8332c8
Source dataset
uspto-grants-2000_12
Patent number
US06166015

Reaction notes

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