Hydrochloric Acid → 5-(3-Bromophenyl)-5-hydroxymethylmorpholin-3-one

HRID 2196209Notes

Reaction equation

HRID 2196209 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:8]([NH:13][C:14](=[O:17])[CH2:15]Cl)([CH2:11][OH:12])[CH2:9][OH:10])[CH:5]=[CH:6][CH:7]=1.CC(O)(C)C.CC(C)([O-])C.[K+].Cl>CC(OC)(C)C.O>[Br:1][C:2]1[CH:3]=[C:4]([C:8]2([CH2:11][OH:12])[NH:13][C:14](=[O:17])[CH2:15][O:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6386tert-ButanolHCID 23665647Potassium tert-butoxideHCID 66665296N-[1-(3-bromophenyl)-2-hydroxy-1-hydroxymethylethyl]-2-chloroacetamide

Product 1

HCID 666654605-(3-Bromophenyl)-5-hydroxymethylmorpholin-3-one

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 15413tert-Butyl methyl etherSolvent

Procedure

A suspension of N-[1-(3-bromo-phenyl)-2-hydroxy-1-hydroxymethyl-ethyl]-2-chloro-acetamide (3.24 g, 10.04 mmol) and 35 ml of t-BuOH was treated with potassium tert-butoxide (1.127 g, 10.04 mmol). The mixture was heated at reflux for 1 h and neutralized with 10 ml of 1N HCl. Water and TBME were added, and the precipitate was filtered off. The organic phase of the filtrate was separated, dried with sodium sulfate and chromatographed on silica gel (EtOAc/MeOH 1-2%) to give the title compound in the form of a colourless solid. TLC (EtOAc/MeOH 1%): Rf=0.23; HPLC: RtH2=2.839 min; 1H-NMR (400 MHz, CD3OD): 7.70 (s, 1H), 7.53-7.47 (m, 2H), 7.35 (t, 1H), 4.17 (s, 2H), 4.08 (d, 1H), 3.98 (d, 1H), 3.91 (d, 1H), 3.87 (d, 1H); MS: 287, 289 [(M+H)+].

Workup

  1. temperatureThe mixture was heated
  2. filtrationthe precipitate was filtered off
  3. customThe organic phase of the filtrate was separated
  4. dry with materialdried with sodium sulfate
  5. customchromatographed on silica gel (EtOAc/MeOH 1-2%)

Sources & evidence

ORD record
ord-4fc8f55dd82f4326a218fd38e5b5f433
Source dataset
uspto-grants-2012_12
Patent number
US08338413B1

Reaction notes

Loading…