Methyl (hydroxymethoxy)acetate → HCID 12859191, compound

HRID 2295461Notes

Reaction equation

HRID 2295461 reaction equation
[NH:1]([CH2:8][C@@H:9]1[CH2:13][CH2:12][CH2:11][NH:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.OCO[CH2:17][C:18]([O:20][CH3:21])=[O:19]>C1C=CC=CC=1>[CH3:21][O:20][C:18]([CH:17]1[N:10]2[CH2:11][CH2:12][CH2:13][CH:9]2[CH2:8][N:1]1[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:19]

Participants

4

Reactant 2

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

Product 1

HCID 12859191HCID 12859191, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A benzene solution containing 541 mg (3.14 mmole) of (S)-2-(anilinomethyl)pyrrolidine and 425 mg (3.45 mmole) of methyl hydroxymethoxyacetate was heated under reflux for 30 minutes while removing formed water azeotropically, to form 3-methoxycarbonyl-2-phenyl-hexahydro-1H-pyrrolo[1,2-c]imidazole. After removing the solvent from the resulting reaction solution, the residue was dissolved in 20 ml of tetrahydrofuran, and 330 mg (3.48 mmole) of anhydrous magnesium chloride was added thereto, followed by heating under reflux for 1 hour. The reaction solution was cooled to -100° C., and a solution of 2-(2,5-dimethoxy-3,4,6-trimethylphenyl)ethylmagnesium bromide in tetrahydrofuran was added dropwise thereto. Completion of the reaction was examined by thin layer chromatography. Thereafter, a saturated aqueous ammonium chloride solution and ether were added, and the organic layer was separated, dried over sodium sulfate and freed from the solvent by evaporation. The residue was purified on alumina column to obtain 730 mg (55%) of 3-[3-(2,5-dimethoxy-3,4,6-trimethylphenyl)propanoyl]-2-phenyl-hexahydro-1H-pyrrolo[1,2-c]imidazole.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 30 minutes
  3. customwhile removing
  4. customformed water azeotropically

Sources & evidence

ORD record
ord-a01400e2856847ef806969c54f5200cd
Source dataset
uspto-grants-1984_01
Patent number
US04424389

Reaction notes

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