Methanol → HCID 67885898, compound

HRID 1032083Notes

Reaction equation

HRID 1032083 reaction equation
CO.[C:3]([OH:8])(=[O:7])[C:4]([OH:6])=[O:5].C1(C(C2C=CC=CC=2)[N:16]2[CH2:19][C@@H:18]([O:20][C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([F:30])([F:29])[F:28])[CH:22]=3)[C@@H:17]2[CH3:31])C=CC=CC=1.[OH-].[NH4+]>O>[C:3]([OH:8])(=[O:7])[C:4]([OH:6])=[O:5].[CH3:31][C@H:17]1[C@H:18]([O:20][C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([F:29])([F:28])[F:30])[CH:22]=2)[CH2:19][NH:16]1

Participants

5

Reactant 3

HCID 887MethanolHCID 14923Ammonium HydroxideHCID 67885528HCID 67885528, compound

Product 1

HCID 67885898HCID 67885898, compoundYield 122.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A methanol-warm water solution of 33 g (0.068 mole) of trans-1-diphenylmethyl-2-methyl-3-[3-(trifluoromethyl)phenoxy]azetidine oxalate was treated with ammonium hydroxide until basic, then extracted with 4×150 ml of methylene chloride. The combined methylene chloride extracts were washed with water, dried over magnesium sulfate, and concentrated in vacuo to a pale yellow oil. This oil was dissolved in 200 ml of 190 ethanol plus 5 ml of triethylamine and hydrogenated on a Parr apparatus with 3.3 g of 5% palladium-on-charcoal catalyst with a 40 psi atmosphere of hydrogen at 70° C. for 12 hr. After the calculated amount of hydrogen had been absorbed, the catalyst was removed by filtration and the filtrate concentrated in vacuo to yield 26.73 g of crude product. An 8 g portion was converted to the oxalate salt in isopropyl alcohol yielding 6.1 g of fine white powder; m.p. 155°-156° C. Total yield extrapolated from the aliquot converted to the oxalate salt was 84% of theory.

Workup

  1. extractionthen extracted with 4×150 ml of methylene chloride
  2. washThe combined methylene chloride extracts were washed with water
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo to a pale yellow oil
  5. dissolutionThis oil was dissolved in 200 ml of 190 ethanol plus 5 ml of triethylamine
  6. customAfter the calculated amount of hydrogen had been absorbed
  7. customthe catalyst was removed by filtration
  8. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-13e5c05417d845dab0d9eb50043bf1fa
Source dataset
uspto-grants-1990_09
Patent number
US04956359

Reaction notes

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