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

HRID 593335Notes

Reaction equation

HRID 593335 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. 4.18 g (88%) of (RS)-5-(3-bromo-phenyl)-5-methyl-morpholin-3-one were obtained as a white solid. Mass (calculated) C11H12BrNO2 [270.128]; (found) [M+H]+=270 and [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-a21957b6e82846cea0a987a0688435e0
Source dataset
uspto-grants-2016_01
Patent number
US09242943B2

Reaction notes

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