Sodium hydride → HCID 68505590, compound

HRID 1716571Notes

Reaction equation

HRID 1716571 reaction equation
[OH:1][C@H:2]1[C@H:7]([N:8]2[C:12]3[CH:13]=[CH:14][C:15]([CH3:17])=[CH:16][C:11]=3[N:10]=[C:9]2[CH3:18])[CH2:6][CH2:5][N:4]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:3]1.[H-].[Na+].Br[CH2:29][C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31].[NH4+].[Cl-]>C1COCC1>[C:22]([O:21][C:19]([N:4]1[CH2:5][CH2:6][CH:7]([N:8]2[C:12]3[CH:13]=[CH:14][C:15]([CH3:17])=[CH:16][C:11]=3[N:10]=[C:9]2[CH3:18])[CH:2]([O:1][CH2:29][C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:3]1)=[O:20])([CH3:25])([CH3:24])[CH3:23]

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 79177tert-Butyl bromoacetateHCID 68514185HCID 68514185, compound

Product 1

HCID 68505590HCID 68505590, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A stirring solution of racemic trans-3-hydroxy-4-[2,5-dimethylbenzimidazol-1yl]-N-Boc-piperidine (950 mg; 2.75 mmol) in THF (30 mL) under Ar cooled to 0° C. NaH (60% oil dispersion; 132 mg; 3.3 mmol) was added and the mixture was stirred for 15 min followed by addition of tert-butyl bromoacetate (516 μL; 3.5 mmol). The reaction mixture was warmed to rt and allowed to stir for 14 hours after which it was poured into satd 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. Racemic 3-tert-butoxycarbonylmethoxy-4-(2,5-dimethyl-benzoimidazol-1-yl)-piperidine-1-carboxylic acid tert-butyl ester was isolated as an oil by flash chromatography (470 mg; 37%)

Workup

  1. stirringto stir for 14 hours after which it
  2. extractionextracted three times with ethyl acetate
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationFiltration
  6. customfollowed by removal of volatiles under reduced pressure
  7. customyielded crude product

Sources & evidence

ORD record
ord-d746fe0ea29f4a31957d271e4fff0ced
Source dataset
uspto-grants-2010_09
Patent number
US07803816B2

Reaction notes

Loading…