Triethylamine → tert-butyl 4-(4-bromo-1-(2-((methylsulfonyl)oxy)ethyl)-1H-imidazol-2-yl)piperidine-1-carboxylate

HRID 2283942Notes

Reaction equation

HRID 2283942 reaction equation
[Br:1][C:2]1[N:3]=[C:4]([CH:10]2[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][CH2:11]2)[N:5]([CH2:7][CH2:8][OH:9])[CH:6]=1.CCN(CC)CC.[S:30](Cl)([CH3:33])(=[O:32])=[O:31]>C(Cl)Cl>[Br:1][C:2]1[N:3]=[C:4]([CH:10]2[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][CH2:11]2)[N:5]([CH2:7][CH2:8][O:9][S:30]([CH3:33])(=[O:32])=[O:31])[CH:6]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 67265139tert-Butyl 4-(4-bromo-1-(2-hydroxyethyl)-1H-imidazol-2-yl)piperidine-1-carboxylate

Product 1

HCID 86641601tert-butyl 4-(4-bromo-1-(2-((methylsulfonyl)oxy)ethyl)-1H-imidazol-2-yl)piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of tert-butyl 4-(4-bromo-1-(2-hydroxyethyl)-1H-imidazol-2-yl)piperidine-1-carboxylate (22.0 g) and Et3N (24.5 ml) in DCM (250 ml) and cool to 0° C. Mesyl chloride (6.8 ml) was added dropwisely and the resulting mixture was stirred for 1 h. The reaction was quenched with saturated aqueous NaHCO3 and extracted with DCM. The organic layer was concentrated to give tert-butyl 4-(4-bromo-1-(2-((methylsulfonyl)oxy)ethyl)-1H-imidazol-2-yl)piperidine-1-carboxylate (28.0 g).

Workup

  1. customThe reaction was quenched with saturated aqueous NaHCO3
  2. extractionextracted with DCM
  3. concentrationThe organic layer was concentrated

Sources & evidence

ORD record
ord-3c69ae5ab7124e2cb88ddfba6b13524d
Source dataset
uspto-grants-2015_09
Patent number
US09145392B2

Reaction notes

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