Methanol → 4-Methyl-4-(pyrrolidin-1-ylmethyl)oxazolidin-2-one

HRID 1023488Notes

Reaction equation

HRID 1023488 reaction equation
Cl[CH2:2][C:3]1([CH3:9])[CH2:7][O:6][C:5](=[O:8])[NH:4]1.[NH:10]1[CH2:14][CH2:13][CH2:12][CH2:11]1.[I-].[Na+].CO>C1COCC1.C(Cl)Cl>[CH3:9][C:3]1([CH2:2][N:10]2[CH2:14][CH2:13][CH2:12][CH2:11]2)[CH2:7][O:6][C:5](=[O:8])[NH:4]1

Participants

7

Reactant 4

HCID 887MethanolHCID 5238Sodium IodideHCID 31268PyrrolidineHCID 553038834-Chloromethyl-4-methyl-oxazolidin-2-one

Product 1

HCID 593551754-Methyl-4-(pyrrolidin-1-ylmethyl)oxazolidin-2-oneYield 35.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
85 °C

Procedure

To a solution of 4-(chloromethyl)-4-methyloxazolidin-2-one (1.41 g, 9.43 mmol) in THF (40 ml) was added pyrrolidine (5.0 ml, 61 mmol) and sodium iodide (1.03 g, 6.87 mmol). The solution was sealed, heated to 85° C. for 24 h, cooled to RT, filtered, and concentrated in vacuo. Flash chromatography (2%→12% MeOH in CH2Cl2) afforded the oxazolidinone (609.8 mg, 3.31 mmol, 35%) as a brown oil which solidified upon standing. The dihydrooxazole was isolated in roughly 75% purity (1.8 g crude yield) and was characterized only by MS. 1H NMR (CDCl3, 400 MHz) δ 1.35 (s, 3H), 1.7-1.8 (m, 4H), 2.5-2.7 (m, 6H), 4.02 (d, J=8.4 Hz, 1H), 4.24 (d, J=8.4 Hz, 1H), 5.3-5.4 (br s, 1H). ESI/APCI expected for C9H16N2O2: 184.12. Found: 185 (MH+). 1H NMR (CDCl3, 400 MHz) δ 1.35 (s, 3H), 1.7-1.8 (m, 4H), 2.5-2.7 (m, 6H), 4.02 (d, J=8.4 Hz, 1H), 4.24 (d, J=8.4 Hz, 1H), 5.3-5.4 (br s, 1H). ESI/APCI expected for C9H16N2O2: 184.12. Found: 185 (MH+).

Workup

  1. customThe solution was sealed
  2. temperaturecooled to RT
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-82e5ea178f114a5790fe42d3ab366654
Source dataset
uspto-grants-2014_05
Patent number
US08722715B2

Reaction notes

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