Dichloromethane → HCID 59224642, compound

HRID 1811761Notes

Reaction equation

HRID 1811761 reaction equation
ClCCl.[NH2:4][CH2:5][C:6]1([CH2:10][NH2:11])[CH2:9][O:8][CH2:7]1.[C:12]1([C:18](Cl)([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(=O)(O)[O-].[Na+]>O>[NH2:4][CH2:5][C:6]1([CH2:10][NH:11][C:18]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH2:9][O:8][CH2:7]1

Participants

6

Reactant 4

HCID 6344Dichloromethane2×HCID 6456Trityl chlorideHCID 516892Sodium BicarbonateHCID 10953471[3-(Aminomethyl)oxetan-3-yl]methanamine

Product 1

HCID 59224642HCID 59224642, compoundYield 51.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

A dichloromethane suspension (3.0 ml) of C-(3-aminomethyloxetan-3-yl)methylamine (411 mg, 3.54 mmol) prepared according to the method described in J. Org. Chem., (1985),50(17), 3211; and Japanese Patent Application Kokai Publication No. (JP-A) S61-69784 (unexamined, published Japanese patent application) was cooled to 0° C., and a dichloromethane solution (3.0 ml) of triphenylmethyl chloride (246 mg, 0.88 mmol) was added thereto. The mixture was stirred at 0° C. for 30 minutes, and then at room temperature for one hour. A saturated aqueous sodium bicarbonate solution (1.0 ml) and water (15 ml) were added to the solution. The mixture was extracted three times with dichloromethane (20 ml). The organic layers were combined together, and dried over anhydrous sodium sulfate. After the inorganic salt was removed by filtration, the filtrate was concentrated under reduced pressure. The resulting crude product was purified by silica gel column chromatography (developing solvent: dichloromethane:methanol=20:1) to yield (3-aminomethyloxetan-3-ylmethyl)tritylamine (162 mg) as a white amorphous material.

Workup

  1. waitat room temperature for one hour
  2. extractionThe mixture was extracted three times with dichloromethane (20 ml)
  3. dry with materialdried over anhydrous sodium sulfate
  4. customAfter the inorganic salt was removed by filtration
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe resulting crude product was purified by silica gel column chromatography (developing solvent: dichloromethane:methanol=20:1)

Sources & evidence

ORD record
ord-96aa38a88ec24c3e87f218f6d9b295b3
Source dataset
uspto-grants-2013_01
Patent number
US08362236B2

Reaction notes

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