Ammonium Chloride → HCID 68510105, compound

HRID 1716572Notes

Reaction equation

HRID 1716572 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[C:18]3[CH:19]=[CH:20][C:21]([CH3:23])=[CH:22][C:17]=3[N:16]=[C:15]2[CH3:24])[CH:10]([O:25]CC(OC(C)(C)C)=O)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C[Mg+].[Br-].[NH4+].[Cl-]>C1COCC1>[OH:5][C:1]([CH3:4])([CH3:3])[CH2:2][O:25][C@H:10]1[C@H:11]([N:14]2[C:18]3[CH:19]=[CH:20][C:21]([CH3:23])=[CH:22][C:17]=3[N:16]=[C:15]2[CH3:24])[CH2:12][CH2:13][N:8]([C:6]([O:5][C:1]([CH3:3])([CH3:2])[CH3:4])=[O:7])[CH2:9]1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 68505590HCID 68505590, compoundHCID 178418689HCID 178418689, compound

Product 1

HCID 68510105HCID 68510105, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Racemic 3-tert-butoxycarbonylmethoxy-4-(2,5-dimethyl-benzoimidazol-1-yl)-piperidine-1-carboxylic acid tert-butyl ester (470 mg; 1.02 mmol) in THF (10 mL) was treated with CH3MgBr (1.0 M in THF; 3 mL, 3 mmol). The reaction mixture was allowed to stir for 1 h and then poured into saturated NH4Cl and extracted three times with ethyl acetate. The combined organic layers were washed with brine and dried over MgSO4. Filtration followed by removal of volatiles under reduced pressure yielded crude product. trans-3-[2-Hydroxy-2-methylpropoxy]-4-[2,5-dimethylbenzimidazol-1yl]-N-Boc-piperidine was isolated by flash chromatography as an oil (324 mg; 78%).

Workup

  1. extractionextracted three times with ethyl acetate
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationFiltration
  5. customfollowed by removal of volatiles under reduced pressure
  6. customyielded crude product

Sources & evidence

ORD record
ord-259b328d3e0944c5bdcdf558c217432a
Source dataset
uspto-grants-2010_09
Patent number
US07803816B2

Reaction notes

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