Imidazole → HCID 22662878, compound

HRID 392495Notes

Reaction equation

HRID 392495 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14]OS(C)(=O)=O)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[NH:22]1[CH:26]=[CH:25][N:24]=[CH:23]1>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][N:22]2[CH:26]=[CH:25][N:24]=[CH:23]2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 24758Sodium hydrideHCID 2765838Tert-butyl 4-(methylsulfonyloxymethyl)piperidine-1-carboxylate

Product 1

HCID 22662878HCID 22662878, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
60 °C

Procedure

A solution of the title compound from Step B (1.0 g, 3.408 mmoles) in DMF (15 mL) was added to a stirred solution of NaH (0.27 g, 6.817 mmoles) and imidazole (0.464 g, 6.817 mmoles) in DMF (15 mL) under nitrogen atmosphere. The mixture was stirred at 60° C. for 16 h. DMF was evaporated in vacuo. The resulting crude product was extracted with CH2Cl2 and the extract was successively washed with water and brine, and the CH2Cl2 was evaporated to leave the title residue which was chromatographed on silica gel using 3% (10% conc NH4OH in methanol)-CH2Cl2 as eluant to give the title compound (0.823 g). FABMS (M+1)=266.2, δH (CDCl3) 0.8-1.0 (m, 2H), 1.2 (s, 9H), 1.2-1.4 (m, 1H), 1.65 (m, 1H), 2.4 (dt, 2H), 3.6 (d, 2H), 4.8 (d, 2H), 6.7 (s, 1H), 6.8 (s, 1H), 7.2 (s, 1H).

Workup

  1. customDMF was evaporated in vacuo
  2. extractionThe resulting crude product was extracted with CH2Cl2
  3. washthe extract was successively washed with water and brine
  4. customthe CH2Cl2 was evaporated

Sources & evidence

ORD record
ord-4ca7a30edd8d4768a3160313f66b6a5d
Source dataset
uspto-grants-2004_10
Patent number
US06800636B2

Reaction notes

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