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

HRID 1159498Notes

Reaction equation

HRID 1159498 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-9204a1fafb2b474481e9e05632f2c4e7
Source dataset
uspto-grants-2010_10
Patent number
US07812178B2

Reaction notes

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