Acrylonitrile → (R)-3-(2-(Hydroxymethyl)pyrrolidin-1-yl)propanenitrile

HRID 2373243Notes

Reaction equation

HRID 2373243 reaction equation
[OH:1][CH2:2][C@H:3]1[CH2:7][CH2:6][CH2:5][NH:4]1.[C:8](#[N:11])[CH:9]=[CH2:10]>C(Cl)Cl>[OH:1][CH2:2][C@H:3]1[CH2:7][CH2:6][CH2:5][N:4]1[CH2:10][CH2:9][C:8]#[N:11]

Participants

4

Reactant 2

HCID 7855AcrylonitrileHCID 2724541Prolinol, (R)-

Product 1

HCID 45088390(R)-3-(2-(Hydroxymethyl)pyrrolidin-1-yl)propanenitrile

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(R)-2-hydroxymethylpyrrolidine (Tokyo Kasei Kogyo Co., Ltd.) (50 g) was dissolved in methylene chloride (500 mL), and acrylonitrile (36 mL) was added dropwise to the solution with stirring at room temperature Subsequently, the mixture was stirred overnight at room temperature. After the completion of the reaction, the solvent was concentrated to give (R)-3-(2-hydroxymethylpyrrolidin-1-yl)propionitrile (76 g).

Workup

  1. stirringthe mixture was stirred overnight at room temperature
  2. customAfter the completion of the reaction
  3. concentrationthe solvent was concentrated

Sources & evidence

ORD record
ord-71c17c9bc58a4d93a32b543866158789
Source dataset
uspto-grants-2008_12
Patent number
US07459465B2

Reaction notes

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