Hydrogen Bromide → (1S,4S)-2-Benzyl-2,5-Diazabicyclo[2.2.1]heptane

HRID 1031486Notes

Reaction equation

HRID 1031486 reaction equation
C1(C)C=CC(S([N:10]2[CH2:15][C@@H:14]3[CH2:16][C@H:11]2[CH2:12][N:13]3[CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)(=O)=O)=CC=1.Br>C(O)(=O)C>[CH2:17]([N:13]1[CH2:12][C@@H:11]2[CH2:16][C@H:14]1[CH2:15][NH:10]2)[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 14612540(1S,4S)-2-(4-toluenesulfonyl)-5-phenylmethyl-2,5-diazabicyclo[2.2.1]heptane

Product 1

HCID 14612543(1S,4S)-2-Benzyl-2,5-Diazabicyclo[2.2.1]heptaneYield 166.7%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of (1S,4S)-2-(4-toluenesulfonyl)-5-phenylmethyl-2,5-diazabicyclo[2.2.1]heptane (54.9 g) in acetic acid (830 mL) containing hydrobromic acid (30% wt) was heated at 70° C. for 18 h. The reaction mixture was allowed to cool and concentrated under reduced pressure to a final volumen of ca. 300 mL. The precipitate that formed was filtered and washed with acetone to give (1S,4S)-N-benzyl-2,5-diazabicyclo[2.2.1]heptane (50.30 g 91.3%, m.p. 272-275° C.).

Workup

  1. temperatureto cool
  2. concentrationconcentrated under reduced pressure to a final volumen of ca. 300 mL
  3. customThe precipitate that formed
  4. filtrationwas filtered
  5. washwashed with acetone

Sources & evidence

ORD record
ord-7239b673ebf94308b7096a4df8bda548
Source dataset
uspto-grants-1990_09
Patent number
US04954502

Reaction notes

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