Methanol → HCID 86745975, compound

HRID 654083Notes

Reaction equation

HRID 654083 reaction equation
[C:1]1([CH:7]([N:9]2[CH2:12][CH:11](O)[CH2:10]2)[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C-:14]#[N:15].[K+].CO.[C:19]([OH:26])(=[O:25])/[CH:20]=[CH:21]\[C:22]([OH:24])=[O:23]>CC(O)C>[C:19]([OH:26])(=[O:25])/[CH:20]=[CH:21]\[C:22]([OH:24])=[O:23].[C:1]1([CH:7]([N:9]2[CH2:12][CH:11]([C:14]#[N:15])[CH2:10]2)[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 9032Potassium CyanideHCID 444266Maleic AcidHCID 37924881-(1-phenylethyl)azetidin-3-ol

Product 1

HCID 86745975HCID 86745975, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A slurry of methanesulfonate ester of 1-(1-phenylethyl)azetidin-3-ol (60.4 g, 223 mmol), potassium cyanide (43.5 g, 669 mmol) and methanol (350 mol) were allowed to stir at ambient temperature for 72 h. The reaction mixture was filtered and the filtrate was concentrated in vacuo. The residue was partitioned between 300 mL of an aqueous 20% potassium carbonate solution and 400 mL of diethyl ether. The organic layer was separated, dried (MgSO4) and concentrated in vacuo. The residue was chromatographed (SiO2, flash, ethyl acetate/hexane 1:3) to give 25.1 g (56%). A 1-g portion was dissolved in 2-propanol and treated with maleic acid (0.75 g, 6.5 mmol). The resulting solid was recrystallized from 2-propanol to give a white solid, mp 147°-148° C.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe residue was partitioned between 300 mL of an aqueous 20% potassium carbonate solution and 400 mL of diethyl ether
  4. customThe organic layer was separated
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customThe residue was chromatographed (SiO2, flash, ethyl acetate/hexane 1:3)
  8. customto give 25.1 g (56%)
  9. customThe resulting solid was recrystallized from 2-propanol
  10. customto give a white solid, mp 147°-148° C.

Sources & evidence

ORD record
ord-72b9bcb6d1e2410ab7fba703653845d6
Source dataset
uspto-grants-1992_07
Patent number
US05130309

Reaction notes

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