Cyanuric chloride → tert-butyl (2R)-2-cyanopyrrolidine-1-carboxylate

HRID 2243879Notes

Reaction equation

HRID 2243879 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C@@H:9]1[C:13](=O)[NH2:14])=[O:7])([CH3:4])([CH3:3])[CH3:2].N1C(Cl)=NC(Cl)=NC=1Cl>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C@@H:9]1[C:13]#[N:14])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 7954Cyanuric chlorideHCID 2756826D-1-N-Boc-prolinamide

Product 1

HCID 2756788tert-butyl (2R)-2-cyanopyrrolidine-1-carboxylateYield 84.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The title product of Example 10 (10.81 g, 50.45 mmol) and cyanuric chloride (5.58 g, 30.3 mmol) was stirred in DMF (30 mL) for 1 h. The reaction mixture was partitioned between ethyl acetate and water. The organic extracts were washed with aq. sodium carbonate, water, brine dried over sodium sulphate, filtered and concentrated to afford the title product (8.34 g, 84%) as a colourless oil.

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate and water
  2. washThe organic extracts were washed with aq. sodium carbonate, water, brine
  3. dry with materialdried over sodium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-bc86d84ef4504911a8a7d9963b65b34e
Source dataset
uspto-grants-2010_03
Patent number
US07678796B2

Reaction notes

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