Methanesulfonyl chloride → HCID 67085429, compound

HRID 2063706Notes

Reaction equation

HRID 2063706 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:12][CH2:11][CH2:10][C@H:9]2[CH2:13]C#N)=[CH:4][CH:3]=1.[CH3:16][S:17](Cl)(=[O:19])=[O:18]>C(Cl)Cl.O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:12][CH2:11][CH2:10][CH:9]2[CH2:13][S:17]([CH3:16])(=[O:19])=[O:18])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 67085445HCID 67085445, compound

Product 1

HCID 67085429HCID 67085429, compoundYield 105%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

(S)-2-(1-(4-bromophenyl)pyrrolidin-2-yl)acetonitrile: To a solution of 20A (2 g, 7.81 mmol) in methylene chloride (16 mL) at 0° C. was added TEA (2.177 mL, 15.62 mmol), and methanesulfonyl chloride (0.913 mL, 11.71 mmol). After 1 h, the reaction mixture was diluted with water and methylene chloride. The layers were extracted, and the organic layer was dried and concentrated to give 2.6 g of 1-(4-bromophenyl)-2-(methylsulfonylmethyl)pyrrolidine (8.17 mmol, 105% yield) as a brown oil that was used directly in the next step. To a solution of 1-(4-bromophenyl)-2-(methylsulfonylmethyl)pyrrolidine (2.6 g, 8.17 mmol) in DMSO (16 mL) was added NaCN (1.531 g, 31.2 mmol) and the resultant mixture was stirred at 50° C. overnight. The reaction mixture was diluted with EtOAc and water. The layers were extracted, and the organic layer was washed successively with water and brine. The organic layer was dried and concentrated, and the resulting material was purified via silica gel chromatography to give 20B (brown oil, 2.1 g, 7.92 mmol, 101% yield). Anal Calc'd for C12H13BrN2 264.03. found [M+H]=264.9, 266.9.

Workup

  1. extractionThe layers were extracted
  2. customthe organic layer was dried
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-3014342705354ad284ac17d8e3222e9c
Source dataset
uspto-grants-2012_10
Patent number
US08288404B2

Reaction notes

Loading…