Methyl formate → HCID 67945511, compound

HRID 1650967Notes

Reaction equation

HRID 1650967 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH:12]([NH2:19])[CH2:13][CH2:14][CH2:15][CH2:16][O:17][CH3:18])[CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[CH:20](OC)=O.[C:24]([OH:31])(=[O:30])/[CH:25]=[CH:26]\[C:27]([OH:29])=[O:28]>CCOCC>[C:24]([OH:31])(=[O:30])/[CH:25]=[CH:26]\[C:27]([OH:29])=[O:28].[CH3:20][NH:19][CH:12]([C:8]1([C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)[CH2:9][CH2:10][CH2:11]1)[CH2:13][CH2:14][CH2:15][CH2:16][O:17][CH3:18]

Participants

5

Reactant 3

HCID 7865Methyl formateHCID 444266Maleic AcidHCID 56609233HCID 56609233, compound

Product 1

HCID 67945511HCID 67945511, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
50 °C

Procedure

A mixture of 1-[1-(4-chlorophenyl)cyclobutyl]-5-methoxypentylamine [1.7 g prepared in a similar manner to that described in method D hereinbefore (X=Cl, R=3, S=1, T=0.67)] and methyl formate (20 ml) was allowed to stand at ambient temperature for 7 days. The mixture was then filtered to remove a colourless solid which was discarded. The filtrate was evaporated and the residue was dissolved in dry toluene (29 ml). The solution was added dropwise to a 70% solution of bis-(2-methoxyethoxy)aluminium hydride in toluene sold under the trade name Red-Al (4.3 ml) in dry toluene (11 ml) under nitrogen and then the reaction mixture was heated to 50° C. with stirring for 3 hours. The reaction mixture was cooled, and water (20 ml) and 5N sodium hydroxide (15 ml) were added. The aqueous layer was separated and extracted with ether and the extracts combined with the toluene solution, washed with water, dried, filtered and evaporated to give an oil which was dissolved in ether. A solution of maleic acid (0.33 g) in ether was added to give a solid which was recrystallised from propan-2-ol to give N-methyl-1-[1-(4-chlorophenyl)cyclobutyl]-5-methoxypentylamine maleate (m.p. 94°-95° C.).

Workup

  1. customprepared in a similar manner to that
  2. filtrationThe mixture was then filtered
  3. customto remove a colourless solid which
  4. customThe filtrate was evaporated
  5. dissolutionthe residue was dissolved in dry toluene (29 ml)
  6. additionThe solution was added dropwise to a 70% solution of bis-(2-methoxyethoxy)aluminium hydride in toluene
  7. temperatureThe reaction mixture was cooled
  8. additionwater (20 ml) and 5N sodium hydroxide (15 ml) were added
  9. customThe aqueous layer was separated
  10. extractionextracted with ether
  11. washwashed with water
  12. customdried
  13. filtrationfiltered
  14. customevaporated
  15. customto give an oil which
  16. customto give a solid which
  17. customwas recrystallised from propan-2-ol

Sources & evidence

ORD record
ord-98d992968a2a48a586d1a3d2a3a77d9e
Source dataset
uspto-grants-1990_05
Patent number
US04925879

Reaction notes

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