Methyl (hydroxymethoxy)acetate → HCID 12859191, compound

HRID 851240Notes

Reaction equation

HRID 851240 reaction equation
OCO[CH2:4][C:5]([O:7][CH3:8])=[O:6].[NH:9]([CH2:16][C@@H:17]1[CH2:21][CH2:20][CH2:19][NH:18]1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>C1C=CC=CC=1>[C:5]([CH:4]1[N:9]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:16][CH:17]2[N:18]1[CH2:19][CH2:20][CH2:21]2)([O:7][CH3:8])=[O:6]

Participants

4

Reactant 2

HCID 88226Methyl (hydroxymethoxy)acetateHCID 6950385(S)-(+)-2-(Anilinomethyl)pyrrolidine

Product 1

HCID 12859191HCID 12859191, compoundYield 98.8%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

In 10 ml of benzene, were dissolved 683 mg of methyl hydroxymethoxyacetate and 1.00 g of (S)-2-(anilinomethyl)pyrrolidine. The resulting solution was refluxed for 30 minutes while removing the water by azeotropic distillation. On removing the solvent by distillation in vacuo, there were obtained 1.38 g of 2-carbomethoxy-3-phenyl-1,3-diazabicyclo[3,3,0]octane, a derivative of glyoxylic acid. NMR peaks: δ(ppm)=1.5-2.3 (4H, multiplet), 2.3-4.1 (5H, multiplet), 3.5 (3H, singlet), 4.6 (1H, singlet), 6.2-7.1 (5H, multiplet). After having been purified by alumina column chromatography and short-path distillation, the substance showed the following results of elementary analysis:

Workup

  1. temperatureThe resulting solution was refluxed for 30 minutes
  2. customwhile removing the water
  3. distillationby azeotropic distillation
  4. customOn removing the solvent
  5. distillationby distillation in vacuo

Sources & evidence

ORD record
ord-5a2b852fea884079a26293ae9a9bee01
Source dataset
uspto-grants-1983_05
Patent number
US04383122

Reaction notes

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