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

HRID 1946903Notes

Reaction equation

HRID 1946903 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.CC([O-])(C)C.[K+].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

5

Reactant 3

HCID 887MethanolHCID 23665647Potassium tert-butoxideHCID 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 tert-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. MS (ISP): m/z=270.1 [M+H]+, 272.2 [M+2+H]+.

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-32efdedf02074fe1b9719abf51933ff6
Source dataset
uspto-grants-2013_03
Patent number
US08399459B2

Reaction notes

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