Dimethyl Sulfoxide → HCID 66653098, compound

HRID 1524258Notes

Reaction equation

HRID 1524258 reaction equation
[NH:1]1[CH2:5][CH2:4][C@@H:3]([OH:6])[CH2:2]1.F[C:8]1[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][CH:9]=1.CS(C)=O.C([O-])([O-])=O.[K+].[K+]>O>[OH:6][C@@H:3]1[CH2:4][CH2:5][N:1]([C:8]2[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][CH:9]=2)[CH2:2]1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 11430Potassium CarbonateHCID 145174-FluorobenzonitrileHCID 2759337(R)-3-Pyrrolidinol

Product 1

HCID 66653098HCID 66653098, compoundYield 99.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Dissolve (R)-pyrrolidin-3-ol (0.08 mL, 1.00 mmol) and 4-fluorobenzonitrile (121 mg, 1.00 mmol) into 1 mL of DMSO. Add K2CO3 (276 mg, 2.00 mmol) and heat the mixture at 120° C. for 16 h. LC-MS analysis indicates the desired intermediate. Add 10 mL of H2O. Filter the precipitate and dry in a Buchner funnel for 1 h to give 188 mg of 4-((R)-3-hydroxy-pyrrolidin-1-yl)-benzonitrile.

Workup

  1. filtrationFilter the precipitate
  2. customdry in a Buchner funnel for 1 h

Sources & evidence

ORD record
ord-1218cdf3769e4a95b894c7ec7dec5030
Source dataset
uspto-grants-2015_07
Patent number
US09079880B2

Reaction notes

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