Imidazole → HCID 58376081, compound

HRID 1942485Notes

Reaction equation

HRID 1942485 reaction equation
[CH2:1]([O:8][C:9]([N:11]([CH:28]([CH3:30])[CH3:29])[C@H:12]1[CH2:17][N:16]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[C@@H:15]([CH2:25][CH2:26][OH:27])[CH2:14][CH2:13]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:31]([Si:35]([C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)([C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)Cl)([CH3:34])([CH3:33])[CH3:32].N1C=CN=C1.C(=O)([O-])O.[Na+]>C(Cl)Cl>[CH2:1]([O:8][C:9]([N:11]([CH:28]([CH3:30])[CH3:29])[C@H:12]1[CH2:17][N:16]([C:18]([O:20][C:21]([CH3:22])([CH3:23])[CH3:24])=[O:19])[C@@H:15]([CH2:25][CH2:26][O:27][Si:35]([C:31]([CH3:34])([CH3:33])[CH3:32])([C:43]2[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=2)[C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[CH2:14][CH2:13]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 94078tert-ButyldiphenylchlorosilaneHCID 516892Sodium BicarbonateHCID 58375893HCID 58375893, compound

Product 1

HCID 58376081HCID 58376081, compoundYield 96.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl (2R,5R)-5-[[(benzyloxy)carbonyl](isopropyl)amino]-2-(hydroxy-ethyl)piperidine-1-carboxylate (2.93 g) in methylene chloride (35 ml) were added tert-butyl diphenyl-chlorosilane (2.30 g) and imidazole (569 mg), and the mixture was stirred at room temperature for 4 hours. To the mixture was added a saturated aqueous sodium hydrogen carbonate solution (10 ml), and the mixture was extracted with chloroform (100 ml). The organic layer was dried over sodium sulfate, filtered, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (the developing solvent: hexane/ethyl acetate=12/1) to give the title compound (4.42 g).

Workup

  1. extractionthe mixture was extracted with chloroform (100 ml)
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (the developing solvent

Sources & evidence

ORD record
ord-32a9241e9e8c4741b42671b0c2c103a0
Source dataset
uspto-grants-2013_03
Patent number
US08389511B2

Reaction notes

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