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

HRID 1352418Notes

Reaction equation

HRID 1352418 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. stirringSubsequently, the mixture was stirred overnight at room temperature
  2. customAfter the completion of the reaction
  3. concentrationthe solvent was concentrated

Sources & evidence

ORD record
ord-56857d1b5a19401ea0a64d48efe4d24c
Source dataset
uspto-grants-2007_05
Patent number
US07220759B2

Reaction notes

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