1,2-Dichloroethane → HCID 69156433, compound

HRID 854282Notes

Reaction equation

HRID 854282 reaction equation
[C:1]([OH:6])(=O)[C:2]([CH3:4])=[O:3].[CH:7]1[CH:8]=[CH:9][C:10]2[N:15](O)N=[N:13][C:11]=2[CH:12]=1.C(Cl)CCl.C(N(CC)CC)C>C(O)(C(F)(F)F)=O.ClCCl>[C:1]([N:13]1[CH2:11][CH2:12][CH2:7][C@@H:8]1[CH2:9][C:10]#[N:15])(=[O:6])[C:2]([CH3:4])=[O:3]

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 1060Pyruvic AcidHCID 8471TriethylamineHCID 757711-Hydroxybenzotriazole

Product 1

HCID 69156433HCID 69156433, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

[(2R)-1-(carbo-tert-butyloxy)pyrrolidin-2-yl]acetonitrile (1.0 g, 4.75 mmol) was stirred in TFA and dichloromethane (1:1 mixture, 12 mL) at room temperature for 3 hr. The solvent was removed under reduced pressure and the residue was taken up in acetonitrile (25 mL). To this solution was added pyruvic acid (450 mg, 5.0 mmol), followed by HOBT (0.8 g, 6 mmol), EDC (1.0 g, 5.5 mmol), and triethylamine (1.0 mL, 7.0 mmol). The reaction was stirred at room temperature overnight. After removal of solvent, the crude product was purified by flash chromatography on a Biotage® system (silica, 30-90% ethyl acetate in hexanes) to yield [(2R)-1-pyruvoylpyrrolidin-2-yl]acetonitrile as yellow oil. MS (M+Na): 203.2

Workup

  1. customThe solvent was removed under reduced pressure
  2. customAfter removal of solvent
  3. customthe crude product was purified by flash chromatography on a Biotage® system (silica, 30-90% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-3a34604cb06f4fe18c967fa8be5da321
Source dataset
uspto-grants-2007_08
Patent number
US07259160B2

Reaction notes

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