Acrylonitrile → HCID 68644380, compound

HRID 1352470Notes

Reaction equation

HRID 1352470 reaction equation
Cl.[OH:2][CH2:3][C@@H:4]1[NH:8][CH2:7][C@@H:6]([OH:9])[CH2:5]1.[C:10](#[N:13])[CH:11]=[CH2:12]>C(=O)([O-])[O-].[K+].[K+].C(#N)C>[OH:9][C@@H:6]1[CH2:7][N:8]([CH2:12][CH2:11][C:10]#[N:13])[C@@H:4]([CH2:3][OH:2])[CH2:5]1

Participants

5

Reactant 2

HCID 7855AcrylonitrileHCID 68644206(3S,5R)-5-(HYDROXYMETHYL)PYRROLIDIN-3-OL HCL

Product 1

HCID 68644380HCID 68644380, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 11430Potassium CarbonateSolvent

Procedure

(3S,5R)-5-Hydroxymethylpyrrolidin-3-ol hydrochloride (0.4 g) described in Biochemistry, Vol. 5, pp. 1154–1155 (1966) was dissolved in aqueous potassium carbonate solution (2 mL) and acetonitrile (2 mL). Acrylonitrile (0.5 mL) was added and the mixture was stirred at room temperature for 5 hr. After the completion of the reaction, the reaction mixture was concentrated and the obtained residue was suspended in chloroform-methanol and dried by adding magnesium sulfate. Magnesium sulfate was filtered off and the solvent was concentrated to give 3-[(2R,4S)-4-hydroxy-2-hydroxymethylpyrrolidin-1-yl]propionitrile (0.47 g).

Workup

  1. customAfter the completion of the reaction
  2. concentrationthe reaction mixture was concentrated
  3. customdried
  4. additionby adding magnesium sulfate
  5. filtrationMagnesium sulfate was filtered off
  6. concentrationthe solvent was concentrated

Sources & evidence

ORD record
ord-2244a8fe2aae448c800eb04f3cc90039
Source dataset
uspto-grants-2007_05
Patent number
US07220759B2

Reaction notes

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