Water → HCID 54098220, compound

HRID 1596446Notes

Reaction equation

HRID 1596446 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][C:11]=1[O:12][CH2:13][CH:14]1[CH2:16][O:15]1)[C:7]#[N:8])([O-:3])=[O:2].[CH:17]12[CH2:25][CH:21]([CH2:22][NH:23][CH2:24]1)[CH2:20][N:19]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:18]2.O>CC(O)C>[C:7]([C:6]1[CH:9]=[CH:10][C:11]([O:12][CH2:13][CH:14]([OH:15])[CH2:16][N:23]2[CH2:24][CH:17]3[CH2:25][CH:21]([CH2:20][N:19]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:18]3)[CH2:22]2)=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=1)#[N:8]

Participants

5

Reactant 3

HCID 962WaterHCID 21701979HCID 21701979, compoundHCID 22490264Tert-butyl 3,7-diazabicyclo(3.3.1)nonane-3-carboxylate

Product 1

HCID 54098220HCID 54098220, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

3-Nitro-4-(2-oxiranylmethoxy)benzonitrile (2.9 g; 13.2 mmol; from step (a) above) was added to a stirred solution of tert-butyl 3,7-diazabicyclo[3.3.1]nonane-3-carboxylate (3 g; 13.2 mmol; see Example F above) in IPA:H2O (12.5 mL; 9:1), and the reaction mixture was refluxed for 3 h. Concentration of the reaction mixture and purification by column chromatography (DCM:MeOH; 15:1) gave the title compound in a 54% yield.

Workup

  1. customConcentration of the reaction mixture and purification by column chromatography (DCM:MeOH; 15:1)

Sources & evidence

ORD record
ord-dec66602ec0e4e9cbb07b9bd9eb37f68
Source dataset
uspto-grants-2001_09
Patent number
US06291475B1

Reaction notes

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