Diethylamine → HCID 178464220, compound

HRID 1170431Notes

Reaction equation

HRID 1170431 reaction equation
[Cl-].[Cl-].[Cl-].[Al+3].[CH2:5]([NH:7][CH2:8][CH3:9])[CH3:6].[OH:10][C@@H:11]1[CH2:14][C@H:13]([C:15]([O:17]CC2C=CC=CC=2)=O)[CH2:12]1.C(=O)(O)[O-].[Na+]>ClCCl>[CH2:5]([N:7]([CH2:8][CH3:9])[C:15]([C@H:13]1[CH2:12][C@@H:11]([OH:10])[CH2:14]1)=[O:17])[CH3:6]

Participants

6

Reactant 4

HCID 8021DiethylamineHCID 516892Sodium BicarbonateHCID 6451240Aluminum(III) ChlorideHCID 178525087HCID 178525087, compound

Product 1

HCID 178464220HCID 178464220, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of aluminum trichloride (533 mg, 4 mmol) in dichloromethane (4 mL) were added diethylamine (1.67 mL, 16 mmol) and benzyl cis-3-hydroxycyclobutane carboxylate (413 mg, 2.0 mmol) at 0° C., and then the mixture was stirred at room temperature for 24 hours. To the reaction solution was added saturated aqueous sodium bicarbonate, and the mixture was filtered through celite, and then extracted with ethyl acetate, dried over magnesium sulfate and filtered. The filtrate was evaporated and purified by silica gel column chromatography (n-hexane/ethyl acetate=3/1 to 0/1, ethyl acetate/methanol=9/1) to give the titled compound (321 mg, 94%).

Workup

  1. filtrationthe mixture was filtered through celite
  2. extractionextracted with ethyl acetate
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customThe filtrate was evaporated
  6. custompurified by silica gel column chromatography (n-hexane/ethyl acetate=3/1 to 0/1, ethyl acetate/methanol=9/1)

Sources & evidence

ORD record
ord-e5a281b36f074ee7b77c1f886ba79f2d
Source dataset
uspto-grants-2010_11
Patent number
US07825155B2

Reaction notes

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