Methanol → HCID 70445968, compound

HRID 1981786Notes

Reaction equation

HRID 1981786 reaction equation
C1(C[N:8]2[CH2:12][CH2:11][CH:10]([S:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)(=[O:15])=[O:14])[CH2:9]2)C=CC=CC=1.Cl[C:23]([O:25]C1C=CC=CC=1)=[O:24].C(N([CH2:37][CH3:38])CC)C.[CH3:39][OH:40]>C(Cl)Cl.CCOCC.Br>[C:23]([OH:25])(=[O:24])/[CH:37]=[CH:38]\[C:39]([OH:14])=[O:40].[C:16]1([S:13]([CH:10]2[CH2:11][CH2:12][NH:8][CH2:9]2)(=[O:15])=[O:14])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

8

Reactant 4

HCID 887MethanolHCID 8471TriethylamineHCID 15891Phenyl chloroformateHCID 118087943-(Benzenesulfonyl)-1-benzylpyrrolidine

Product 1

HCID 70445968HCID 70445968, compound

Reagents, catalysts & solvents 3

HCID 260Hydrogen BromideSolventHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent2×

Procedure

A solution of 16.77 g (0.0557 mole) of 1-(phenylmethyl)-3-(phenylsulfonyl)pyrrolidine (free base) and 12.0 g (0.076 mole) of phenyl chloroformate in 500 ml of methylene chloride was stirred at room temperature for 4 hr. The solvent was removed in vacuo to give an oil. The oil was dissolved in ether with a little methyl alcohol and methylene chloride added to clear the solution. An excess of triethylamine was added and the solution stirred for 1 hr. The mixture was filtered and the solvent removed in vacuo from the filtrate to give an oil. This oil was suspended in 300 ml of 48% hydrobromic acid and the mixture was refluxed for 14.5 hr. The reaction mixture was extracted with several portions of ether and the ether layers discarded. The solution was made basic with 50% aqueous sodium hydroxide and the basic solution was extracted with several portions of methylene chloride. The combined methylene chloride extract of the basic solution was dried over magnesium sulfate and the solvent removed in vacuo to give an oil, the free base of the title compound. The free base was converted to the maleate salt, crystallizing and recrystallizing from methyl alcohol-diethyl ether to give 10.53 g (57.8%) of crystalline solid, m.p. 146.5°-147.5° C.

Workup

  1. customThe solvent was removed in vacuo
  2. customto give an oil
  3. additionadded
  4. filtrationThe mixture was filtered
  5. customthe solvent removed in vacuo from the filtrate
  6. customto give an oil
  7. temperaturethe mixture was refluxed for 14.5 hr
  8. extractionThe reaction mixture was extracted with several portions of ether
  9. extractionthe basic solution was extracted with several portions of methylene chloride
  10. extractionThe combined methylene chloride extract of the basic solution
  11. dry with materialwas dried over magnesium sulfate
  12. customthe solvent removed in vacuo
  13. customto give an oil

Sources & evidence

ORD record
ord-aca271fca6bc47b69c6f41ff184e5634
Source dataset
uspto-grants-1986_06
Patent number
US04593102

Reaction notes

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