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

HRID 221675Notes

Reaction equation

HRID 221675 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.[K].[O-]CCCC.Cl>CC(OC)(C)C.O.CC(O)(C)C>[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

8

Reactant 4

HCID 313Hydrochloric AcidHCID 5462222PotassiumHCID 12476378Butan-1-olateHCID 66665296N-[1-(3-bromophenyl)-2-hydroxy-1-hydroxymethylethyl]-2-chloroacetamide

Product 1

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

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6386tert-ButanolSolventHCID 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 tart-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-16eb74ee1e4e49458eca9cc0242540f5
Source dataset
uspto-grants-2012_06
Patent number
US08207164B2

Reaction notes

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