Triethylamine → HCID 67173154, compound

HRID 1891263Notes

Reaction equation

HRID 1891263 reaction equation
[Br:1][C:2]1[CH:13]=[CH:12][C:5]([CH2:6][NH:7][CH2:8][C@H:9]([OH:11])[CH3:10])=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:21](N1C=CN=C1)(N1C=CN=C1)=[O:22]>C1COCC1.O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[CH2:8][C@@H:9]([CH3:10])[O:11][C:21]2=[O:22])=[CH:12][CH:13]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 913938HCID 913938, compound

Product 1

HCID 67173154HCID 67173154, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

(R)-1-(4-bromobenzylamino)propan-2-ol (5F2) (0.034 mol, 8.2 g) was dissolved in THF (150 ml) and triethylamine (0.051 mol, 5.12 g) was added, followed by carbonyldiimidazole (0.037 mol, 6.0 g). The mixture was stirred at room temperature for 2 hours then heated to reflux for 20 hours. The reaction mixture was diluted with water and extracted three times with EtOAc. The combined organics were washed with water and brine before drying over sodium sulphate. The crude mixture was purified on silica eluting with 35% EtOAc/Petroleum Ether to give (R)-3-(4-bromobenzyl)-5-methyloxazolidin-2-one (5F3) 6.7 g (74%); 1H NMR (400 MHz, CDCl3) δ 7.48 (d, 2H) 7.16 (d, 2H) 4.62 (m, 1H) 4.41-4.32 (m, 2H) 3.49 (m, 1H) 2.95 (m, 1H) 1.39 (d, 3H).

Workup

  1. temperaturethen heated
  2. temperatureto reflux for 20 hours
  3. extractionextracted three times with EtOAc
  4. washThe combined organics were washed with water and brine
  5. dry with materialbefore drying over sodium sulphate
  6. customThe crude mixture was purified on silica eluting with 35% EtOAc/Petroleum Ether

Sources & evidence

ORD record
ord-13f2435ab7974e2e8537044511a2bf87
Source dataset
uspto-grants-2013_08
Patent number
US08507521B2

Reaction notes

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