Pyrrolidine → HCID 11681084, compound

HRID 1445787Notes

Reaction equation

HRID 1445787 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][CH:10]=[C:11]([CH2:13]Cl)[N:12]=2)=[CH:4][CH:3]=1.[NH:15]1[CH2:19][CH2:18][CH2:17][CH2:16]1>O1CCCC1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][CH:10]=[C:11]([CH2:13][N:15]3[CH2:19][CH2:18][CH2:17][CH2:16]3)[N:12]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 31268PyrrolidineHCID 155551142-(4-Bromophenyl)-4-(chloromethyl)oxazole2×

Product 1

HCID 11681084HCID 11681084, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-(4-Bromo-phenyl)-4-chloromethyl-oxazole (See Intermediate 1) (0.321 g, 1.18 mmol), and pyrrolidine (0.639 g, 9.0 mmol) are dissolved in 20 mL tetrahydrofuran and stirred at ambient temperature for 1.5 hours. The reaction is concentrated to an oil and redissolved in diethyl ether which is washed with aqueous sodium bicarbonate, water, separated and dried over sodium sulfate, filtered and concentrated to a dark oil. The oil is purified by flash silica gel chromatography (2% 2M NH3 in MeOH/dichloromethane) to give 0.185 g of the titled compound. MS (m/e) (81Br): 309.1 (M+1)

Workup

  1. concentrationThe reaction is concentrated to an oil
  2. dissolutionredissolved in diethyl ether which
  3. washis washed with aqueous sodium bicarbonate, water
  4. customseparated
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated to a dark oil
  8. customThe oil is purified by flash silica gel chromatography (2% 2M NH3 in MeOH/dichloromethane)

Sources & evidence

ORD record
ord-a8e65514e1414b18996a85232f871e97
Source dataset
uspto-grants-2010_02
Patent number
US07666871B2

Reaction notes

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