Benzylamine → (1R,4R)-2-(4-toluenesulfonyl)-5-phenylmethyl-2,5-diazabicyclo[2.2.1]heptane

HRID 1031586Notes

Reaction equation

HRID 1031586 reaction equation
[C:1]1([CH3:38])[CH:6]=[CH:5][C:4]([S:7]([N:10]2[CH2:14][C@@H:13](OS(C3C=CC(C)=CC=3)(=O)=O)[CH2:12][C@@H:11]2[CH2:26]OS(C2C=CC(C)=CC=2)(=O)=O)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[CH2:39]([NH2:46])[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1>C1(C)C=CC=CC=1>[C:1]1([CH3:38])[CH:2]=[CH:3][C:4]([S:7]([N:10]2[CH2:14][C@H:13]3[CH2:12][C@@H:11]2[CH2:26][N:46]3[CH2:39][C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)(=[O:8])=[O:9])=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 7504Benzylamine2×HCID 15629272((2R,4S)-1-[(4-Methylphenyl)sulfonyl]-4-{[(4-methylphenyl)sulfonyl]oxy}pyrrolidinyl)methyl 4-methylbenzenesulfonate

Product 1

HCID 14612539(1R,4R)-2-(4-toluenesulfonyl)-5-phenylmethyl-2,5-diazabicyclo[2.2.1]heptaneYield 90%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 2697 g (4.653 moles) of (2R, 4S)-1-(4-toluenesulfonyl)-2-(4-toluenesulfonyloxymethyl)-4-(4-toluenesulfonyloxy)-pyrrolidine and 1640 g (15.304 moles) of benzylamine in 15 L of toluene was heated under reflux. After 6 hours 100 g of benzylamine were added and the reflux continued for 3 hours. The mixture was cooled, filtered and the residue was washed with 5 L of toluene. The combined organic layers were evaporated to dryness and the resulting solid was taken up with 2 L of isopropanol. After cooling the product was filtered, washed with cold isopropanol and dried under reduced pressure to give 1434 g of the titled compound. (90%). M.P. =124° C. [α]D =-15.72° (c=1.6, acetone)

Workup

  1. temperaturewas heated
  2. temperatureunder reflux
  3. temperatureThe mixture was cooled
  4. filtrationfiltered
  5. washthe residue was washed with 5 L of toluene
  6. customThe combined organic layers were evaporated to dryness
  7. temperatureAfter cooling the product
  8. filtrationwas filtered
  9. washwashed with cold isopropanol
  10. customdried under reduced pressure

Sources & evidence

ORD record
ord-8204a9c9d7cf436bbc7822c9f8621926
Source dataset
uspto-grants-1990_09
Patent number
US04954507

Reaction notes

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