2-Azido-7-[5-(4-fluorophenyl)pyridin-2-yl]-7-azaspiro[3.5]nonane → 7-[5-(4-Fluorophenyl)pyridin-2-yl]-7-azaspiro[3.5]non-2-ylamine

HRID 336539Notes

Reaction equation

HRID 336539 reaction equation
[N:1]([CH:4]1[CH2:7][C:6]2([CH2:12][CH2:11][N:10]([C:13]3[CH:18]=[CH:17][C:16]([C:19]4[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=4)=[CH:15][N:14]=3)[CH2:9][CH2:8]2)[CH2:5]1)=[N+]=[N-]>C(O)C.[Pd].CC([O-])=O.CC([O-])=O.[Pb+2]>[F:25][C:22]1[CH:23]=[CH:24][C:19]([C:16]2[CH:17]=[CH:18][C:13]([N:10]3[CH2:11][CH2:12][C:6]4([CH2:5][CH:4]([NH2:1])[CH2:7]4)[CH2:8][CH2:9]3)=[N:14][CH:15]=2)=[CH:20][CH:21]=1

Participants

4

Reactant 1

HCID 866606422-Azido-7-[5-(4-fluorophenyl)pyridin-2-yl]-7-azaspiro[3.5]nonane

Product 1

HCID 687630337-[5-(4-Fluorophenyl)pyridin-2-yl]-7-azaspiro[3.5]non-2-ylamineYield 63.9%

Reagents, catalysts & solvents 2

HCID 131709914Lindlars catalystCatalystHCID 702EthanolSolvent

Procedure

The process is performed according to the procedure described in Example 6 (step 6.4.). Starting with 6.60 g (19.56 mmol) of 2-azido-7-[5-(4-fluorophenyl)pyridin-2-yl]-7-azaspiro[3.5]nonane, obtained in step 10.4., in 28 mL of ethanol, 0.81 g (3.91 mmol) of Lindlar catalyst (PdCaCO3) is added. 3.89 g of pure product are thus obtained in the form of a yellow powder.

Workup

  1. customobtained in step 10.4

Sources & evidence

ORD record
ord-851c63cd6e724f4591601ae90f253484
Source dataset
uspto-grants-2014_11
Patent number
US08889702B2

Reaction notes

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