Thionyl Chloride → HCID 53828342, compound

HRID 974979Notes

Reaction equation

HRID 974979 reaction equation
O[CH2:2][CH2:3][C@@H:4]1[CH2:8][CH2:7][CH2:6][N:5]1[CH2:9][CH2:10][C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[CH2:16][CH2:15][CH2:14]2.S(Cl)([Cl:22])=O>C(Cl)(Cl)Cl>[Cl:22][CH2:2][CH2:3][C@@H:4]1[CH2:8][CH2:7][CH2:6][N:5]1[CH2:9][CH2:10][C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[CH2:16][CH2:15][CH2:14]2

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 53921776HCID 53921776, compound

Product 1

HCID 53828342HCID 53828342, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of (2S)-(2-hydroxyethyl)-1-[2-(indan-5-yl)ethyl]pyrrolidine (0.99 g, 3.8 mmol--see Preparation 17) and thionyl chloride (1 ml) in chloroform (15 ml) was heated under reflux for 3 hours and evaporated. The residue was partitioned between ethyl acetate and saturated aqueous sodium carbonate solution and the organic layer was dried over magnesium sulphate and evaporated to give the title compound (956 mg, 91%) as a brown oil which was not characterised before use (Example 24).

Workup

  1. temperatureunder reflux for 3 hours
  2. customevaporated
  3. customThe residue was partitioned between ethyl acetate and saturated aqueous sodium carbonate solution
  4. dry with materialthe organic layer was dried over magnesium sulphate
  5. customevaporated

Sources & evidence

ORD record
ord-e050796a898b4481868f5fd56b724aa4
Source dataset
uspto-grants-1997_03
Patent number
US05607950

Reaction notes

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