Dimethylformamide → Tert-butyl 4-[1-(2-pyrrolidin-1-ylethyl)-4-tetrahydropyran-4-yl-imidazol-2-yl]piperidine-1-carboxylate

HRID 2088894Notes

Reaction equation

HRID 2088894 reaction equation
CS(O[CH2:6][CH2:7][N:8]1[CH:12]=[C:11]([CH:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)[N:10]=[C:9]1[CH:19]1[CH2:24][CH2:23][N:22]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:21][CH2:20]1)(=O)=O.[NH:32]1[CH2:36][CH2:35][CH2:34][CH2:33]1.CN(C)C=O>ClCCl.C(=O)(O)[O-].[Na+]>[N:32]1([CH2:6][CH2:7][N:8]2[CH:12]=[C:11]([CH:13]3[CH2:14][CH2:15][O:16][CH2:17][CH2:18]3)[N:10]=[C:9]2[CH:19]2[CH2:24][CH2:23][N:22]([C:25]([O:27][C:28]([CH3:30])([CH3:31])[CH3:29])=[O:26])[CH2:21][CH2:20]2)[CH2:36][CH2:35][CH2:34][CH2:33]1

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 31268PyrrolidineHCID 86666573HCID 86666573, compound

Product 1

HCID 67112170Tert-butyl 4-[1-(2-pyrrolidin-1-ylethyl)-4-tetrahydropyran-4-yl-imidazol-2-yl]piperidine-1-carboxylateYield 93%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
50 °C

Procedure

Combine tert-butyl 4-(1-(2-(methylsulfonyloxy)ethyl)-4-(tetrahydro-2H-pyran-4-yl)-1H-imidazol-2-yl)piperidine-1-carboxylate (2.02 g, 4.42 mmol), pyrrolidine (1.1 mL, 3.0 eq), and dimethylformamide (19 mL). Heat the reaction mixture to 50° C. overnight. Dilute with dichloromethane and saturated aqueous sodium bicarbonate. Separate the layers. Wash the organics with water. Dry the organics over anhydrous sodium sulfate, filter, and concentrate in vacuo. Purify by silica gel chromatography, eluting with hexanes to ethyl acetate to 10% methanol in dichloromethane, to give the title compound as a yellow oil (1.79 g, 93%). MS (ES) m/z=433 [M]+.

Workup

  1. customSeparate the layers
  2. washWash the organics with water
  3. dry with materialDry the organics over anhydrous sodium sulfate
  4. filtrationfilter
  5. concentrationconcentrate in vacuo
  6. customPurify by silica gel chromatography
  7. washeluting with hexanes to ethyl acetate to 10% methanol in dichloromethane

Sources & evidence

ORD record
ord-0c32b50608514a8ca7800a8de4a1c070
Source dataset
uspto-grants-2013_05
Patent number
US08436002B2

Reaction notes

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