Thionyl Chloride → (R)-1-[4-(3-Fluoro-benzyloxy)-phenyl]-5-oxo-pyrrolidine-3-carbonitrile

HRID 273178Notes

Reaction equation

HRID 273178 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:22]=[CH:23][CH:24]=1)[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([N:13]2[C:17](=[O:18])[CH2:16][C@@H:15]([C:19]([NH2:21])=O)[CH2:14]2)=[CH:9][CH:8]=1.S(Cl)(Cl)=O>O1CCCC1>[F:1][C:2]1[CH:3]=[C:4]([CH:22]=[CH:23][CH:24]=1)[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([N:13]2[C:17](=[O:18])[CH2:16][C@@H:15]([C:19]#[N:21])[CH2:14]2)=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 11529971(R)-1-[4-(3-Fluoro-benzyloxy)-phenyl]-5-oxo-pyrrolidine-3-carboxylic acid amide

Product 1

HCID 69309400(R)-1-[4-(3-Fluoro-benzyloxy)-phenyl]-5-oxo-pyrrolidine-3-carbonitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of (R)-1-[4-(3-fluoro-benzyloxy)-phenyl]-5-oxo-pyrrolidine-3-carboxylic acid amide (0.400 g, 0.001 mol) and thionyl chloride (2.3 ml, 0.032 mol) was refluxed under argon for 3 hours. The mixture was cooled to room temperature, diluted with 5 ml tetrahydrofuran, concentrated under vacuum and purified by column chromatography on silica gel using a 2:3-mixture of ethyl acetate and hexane as the eluent. The product fractions were concentrated to dryness to yield (0.106 g, 28% of theory) of a light brown oil. MS (m/e)=311.1 (M+H)+.

Workup

  1. temperaturewas refluxed under argon for 3 hours
  2. concentrationconcentrated under vacuum
  3. custompurified by column chromatography on silica gel using a 2
  4. concentrationThe product fractions were concentrated to dryness
  5. customto yield (0.106 g, 28% of theory) of a light brown oil

Sources & evidence

ORD record
ord-fe8f99057bd24480841b0b0f228d837d
Source dataset
uspto-grants-2008_11
Patent number
US07456210B2

Reaction notes

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