Methanol → 5-(3-Bromophenyl)-5-methylmorpholin-3-one

HRID 1929457Notes

Reaction equation

HRID 1929457 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:8]([NH:12][C:13](=[O:16])[CH2:14]Cl)([CH3:11])[CH2:9][OH:10])[CH:5]=[CH:6][CH:7]=1.[K].CCSC(N(CC(C)C)CC(C)C)=O.CO>CC(O)(CC)C>[Br:1][C:2]1[CH:3]=[C:4]([C:8]2([CH3:11])[NH:12][C:13](=[O:16])[CH2:14][O:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 16181ButylateHCID 5462222PotassiumHCID 58155284N-[1-(3-Bromophenyl)-2-hydroxy-1-methylethyl]-2-chloroacetamide

Product 1

HCID 581553055-(3-Bromophenyl)-5-methylmorpholin-3-oneYield 91%

Reagents, catalysts & solvents 1

HCID 64052-Methyl-2-butanolSolvent

Procedure

A solution of (RS)-N-[1-(3-bromo-phenyl)-2-hydroxy-1-methyl-ethyl]-2-chloro-acetamide (5.36 g, 17 mmol) in 2-methyl-2-butanol (100 ml) was treated in one portion with potassium tent-butylate (6.66 g, 58 mmol). Initially, the temperature rose to 30° C.; the reaction mixture was left to cool to room temperature and stirring was continued for one hour. For the workup, the reaction mixture was treated with methanol (50 ml), then evaporated at reduced pressure. The residue was purified by chromatography on silica gel using a gradient of dichloromethane/methanol=100/0 to 75/25 as the eluent. There were obtained 4.18 g (88% of theory) of (RS)-5-(3-bromo-phenyl)-5-methyl-morpholin-3-one as a white solid. Mass (calculated) C11H12BrNO2 [270.128]; (found) [M+H]+=270, [M+2-H]+==272.

Workup

  1. customrose to 30° C.
  2. waitthe reaction mixture was left
  3. customevaporated at reduced pressure
  4. customThe residue was purified by chromatography on silica gel using a gradient of dichloromethane/methanol=100/0 to 75/25 as the eluent

Sources & evidence

ORD record
ord-4b4d45f8e75542c4ab3273f779f65774
Source dataset
uspto-grants-2012_05
Patent number
US08188079B2

Reaction notes

Loading…