Methyl chloroformate → HCID 86614356, compound

HRID 2265158Notes

Reaction equation

HRID 2265158 reaction equation
C(N(CC)CC)C.[C:8](Cl)(=[O:11])[O:9][CH3:10].[NH2:13][CH2:14][C@@H:15]1[C@@H:20]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[CH3:27])[CH2:19][CH2:18][N:17]([CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH2:16]1.[OH-].[Na+]>C(Cl)(Cl)Cl>[CH2:28]([N:17]1[CH2:18][CH2:19][C@H:20]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[CH3:27])[C@@H:15]([CH2:14][NH:13][C:8](=[O:11])[O:9][CH3:10])[CH2:16]1)[C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

Participants

6

Reactant 4

HCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 68427245HCID 68427245, compound

Product 1

HCID 86614356HCID 86614356, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

111 μL of triethylamine and 37 μL of methyl chlorocarbonate were added to chloroform (2 mL) solution of 93 mg of (3S*,4S*)-3-aminomethyl-1-benzyl-4-o-tolyl-piperidine obtained in Production Example 37, and stirred at room temperature for 50 minutes. Aqueous 1 M sodium hydroxide solution was added to the reaction liquid, and extracted with ethyl acetate. The ethyl acetate layer was washed with saturated saline water, and dried with anhydrous sodium sulfate. The solvent was evaporated off under reduced pressure, and the residue was separated and purified through preparative thin-layer chromatography (chloroform/methanol=20/1) to obtain 78 mg of the entitled compound.

Workup

  1. customobtained in Production Example 37
  2. extractionextracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with saturated saline water
  4. dry with materialdried with anhydrous sodium sulfate
  5. customThe solvent was evaporated off under reduced pressure
  6. customthe residue was separated
  7. custompurified through preparative thin-layer chromatography (chloroform/methanol=20/1)

Sources & evidence

ORD record
ord-684be3ed1f3c410e95dfd93357313fbf
Source dataset
uspto-grants-2010_12
Patent number
US07855294B2

Reaction notes

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