Thionyl Chloride → HCID 86679113, compound

HRID 1774729Notes

Reaction equation

HRID 1774729 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([N:8]2[CH2:12][CH2:11][CH2:10][C@H:9]2[CH2:13]O)[CH:5]=[N:6][CH:7]=1.S(Cl)([Cl:17])=O.C([O-])(O)=O.[Na+]>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[N:6][CH:5]=[C:4]([N:8]2[CH2:12][CH2:11][CH2:10][C@H:9]2[CH2:13][Cl:17])[CH:3]=1

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 86679112HCID 86679112, compound

Product 1

HCID 86679113HCID 86679113, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of (S)-(1-(5-bromopyridin-3-yl)pyrrolidin-2-yl)methanol (0.060 g, 0.233 mmol) in DCM (1 mL) cooled to 0° C. was added thionyl chloride (0.112 g, 0.932 mmol) dropwise. The reaction mixture was stirred at this temperature for 30 min and then allowed to warm up to room temperature and stirring was continued over night. The mixture was diluted with DCM, poured into aq. NaHCO3 (10 mL) and the aqueous layer was extracted with DCM (2×20 mL). Combined organics were washed with brine, dried over Na2SO4, filtered and evaporated to dryness to give the title compound (0.055 g, 86%) as an orange oil. MS: 275.0, 277.0 (M+H+).

Workup

  1. stirringstirring
  2. waitwas continued over night
  3. extractionthe aqueous layer was extracted with DCM (2×20 mL)
  4. washCombined organics were washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-4e2a74611b164300979b29cc6df16949
Source dataset
uspto-grants-2016_02
Patent number
US09260408B2

Reaction notes

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