Pseudoephedrine → (4S,5S)-2-(5-bromo-2,3-dihydrobenzofuran-7-yl)-3,4-dimethyl-5-phenyl-1,3-oxazolidin

HRID 389791Notes

Reaction equation

HRID 389791 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:11]=[O:12])[C:5]2[O:9][CH2:8][CH2:7][C:6]=2[CH:10]=1.[CH3:13][C@H:14]([NH:23][CH3:24])[C@@H:15](O)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C1C=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4]([CH:11]2[N:23]([CH3:24])[C@@H:14]([CH3:13])[C@H:15]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[O:12]2)[C:5]2[O:9][CH2:8][CH2:7][C:6]=2[CH:10]=1

Participants

4

Reactant 2

HCID 7028PseudoephedrineHCID 27948045-Bromo-2,3-dihydrobenzo[b]furan-7-carbaldehyde

Product 1

HCID 67442847(4S,5S)-2-(5-bromo-2,3-dihydrobenzofuran-7-yl)-3,4-dimethyl-5-phenyl-1,3-oxazolidinYield 79%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A sample of 20 (650 mg, 2.9 mmol) and (1S,2S) pseudoephedrine (500 mg, 3.0 mmol) in 40 mL of benzene was refluxed overnight using a Dean-Stark trap. Solvent removal yielded yellow crystals which were recrystallized from a minimum of hot hexanes to give white crystals of 21 (841 mg, 79%), mp=83.5-85.5° C.

Workup

  1. customSolvent removal
  2. customyielded yellow crystals which
  3. customwere recrystallized from a minimum of hot hexanes

Sources & evidence

ORD record
ord-860afc67fc3a4393b51aabc611d574c0
Source dataset
uspto-grants-2013_02
Patent number
US08383083B2

Reaction notes

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