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

HRID 981986Notes

Reaction equation

Br.Br.[CH2:3]([N:10]1[CH2:15][C@@H:14]2[CH2:16][C@H:11]1[CH2:12][NH:13]2)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C1(C)C=CC(S(N2C[C@@H]3C[C@H]2CN3CC2C=CC=CC=2)(=O)=O)=CC=1.Br>CC(O)=O>[CH2:3]([N:10]1[CH2:15][C@@H:14]2[CH2:16][C@H:11]1[CH2:12][NH:13]2)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

Conditions

Temperature: 70 °C

Procedure

(1S,4S)-N-benzyl-2,5-diazabicyclo[2.2.1]heptane dihydrobromide. A mixture of (1S,4S)-2-(4-toluenesulfonyl)-5-phenylmethyl-2,5-diazabicyclo[2.2.1]heptane (54.0 g, 0.16 mole) in AcOH (830 mL) containing HBr (30% wt.) was heated at 70° C. for 1% h. The reaction mixture was allowed to cool and concentrated under reduced pressure to a final volume 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

temperatureto cool
concentrationconcentrated under reduced pressure to a final volume of ca. 300 mL
customThe precipitate that formed
filtrationwas filtered
washwashed with acetone

Sources & evidence

ORD record: ord-0763b6d511c342d8ad1cd2a964f6de2e
Source dataset: uspto-grants-1991_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04994460

Reaction notes

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