Thionyl Chloride → HCID 51063834, compound

HRID 1508324Notes

Reaction equation

HRID 1508324 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:8]2[C:12](=O)[CH2:11][CH:10]([C:14]([O:16]C)=[O:15])[CH2:9]2)[CH:5]=[CH:6][CH:7]=1.S(Cl)(Cl)=O>CO>[Cl:1][C:2]1[CH:3]=[C:4]([N:8]2[CH2:12][CH2:11][CH:10]([C:14]([OH:16])=[O:15])[CH2:9]2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 10377591HCID 10377591, compound

Product 1

HCID 51063834HCID 51063834, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 1-(3-chlorophenyl)-5-oxopyrrolidine-3-carboxylate (Ref: Tetrahedron, 62:4011-4017 (2006)). To a cold solution of MeOH (8.35 mL) (0° C.) was added thionyl chloride (0.335 mL, 4.59 mmol) dropwise. After 30 min, Intermediate 10 (1 g, 4.17 mmol) was added, and the reaction mixture was warmed to rt. The reaction mixture was then concentrated and the residue dissolved in EtOAc, washed with saturated NaHCO3, H2O and brine. The organic layers were dried over Na2SO4, filtered and concentrated to yield the desired product (1.04 g, 98%) as yellow oil. MS(ESI) m/z: 254.0 (M+H)+.

Workup

  1. concentrationThe reaction mixture was then concentrated
  2. dissolutionthe residue dissolved in EtOAc
  3. washwashed with saturated NaHCO3, H2O and brine
  4. dry with materialThe organic layers were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-a6f73162d43c411988544ba535be9cfa
Source dataset
uspto-grants-2015_12
Patent number
US09221818B2

Reaction notes

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