2-Azido-9-benzyl-6-bromo-9-azabicyclo[3.3.1]nonane → 2-Benzyl-2,7-diaza-tricyclo-[4.4.0.03,8]decane

HRID 1912337Notes

Reaction equation

HRID 1912337 reaction equation
[N:1]([CH:4]1[CH2:11][CH2:10][CH:9](Br)[CH:8]2[N:13]([CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH:5]1[CH2:6][CH2:7]2)=[N+]=[N-].N(C1CCC2N(CC3C=CC=CC=3)C1CCC2Br)=[N+]=[N-]>>[CH2:14]([N:13]1[CH:9]2[CH:8]3[NH:1][CH:4]([CH2:11][CH2:10]2)[CH:5]1[CH2:6][CH2:7]3)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

3

Reactant 2

HCID 508962802-Azido-9-benzyl-6-bromo-9-azabicyclo[3.3.1]nonaneHCID 508962822-Azido-9-benzyl-5-bromo-9-azabicyclo-[4.2.1]nonane

Product 1

HCID 508962842-Benzyl-2,7-diaza-tricyclo-[4.4.0.03,8]decaneYield 68%

Procedure

The synthesis described in Ex. 2.1 was repeated, but substituting the azide (1.1A) with the compound (1.1B) obtained in Ex. 1.1. The compound 2-benzyl-2,7-diaza-tricyclo-[4.4.0.03,8]decane is obtained. Yield: 68%. 1H-NMR (CDCl3) δ 1.50-2.00 (m, 8H); 2.70-2.80 (m, 2H); 3.00-3.10 (m, 2H); 3.90 (AB system, 2H, J=13.8 Hz); 7.20-7.42 (m, 5H). Anal. calc. for C15H20N2: C, 78.90; H, 8.83; N, 12.27. Found: C, 78.78; H, 8.81; N, 12.26.

Workup

  1. customobtained in Ex

Sources & evidence

ORD record
ord-1f200cc16f724a6eb0e0e06bba2571f9
Source dataset
uspto-grants-2013_12
Patent number
US08609659B2

Reaction notes

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