Trifluoroacetic acid → N-(6-methyl-2-pyridinyl)-8-azaspiro[4.5]decane-7-methanamine

HRID 536595Notes

Reaction equation

[CH3:1][C:2]1[N:7]=[C:6]([NH:8][CH2:9][CH:10]2[N:19](C(OC(C)(C)C)=O)[CH2:18][CH2:17][C:12]3([CH2:16][CH2:15][CH2:14][CH2:13]3)[CH2:11]2)[CH:5]=[CH:4][CH:3]=1.FC(F)(F)C(O)=O>ClCCl>[CH2:13]1[C:12]2([CH2:17][CH2:18][NH:19][CH:10]([CH2:9][NH:8][C:6]3[CH:5]=[CH:4][CH:3]=[C:2]([CH3:1])[N:7]=3)[CH2:11]2)[CH2:16][CH2:15][CH2:14]1

Participants

Conditions

Temperature: 0 °C

Procedure

(±)tert-butyl 7-(((6-methylpyridin-2-yl)amino)methyl)-8-azaspiro[4.5]decane-8-carboxylate (intermediate 73, 1.3 g, 3.62 mmol) was dissolved in dichloromethane (10 ml) and cooled to 0° C., then trifluoroacetic acid (30 ml) was added. After 1 hour at 0° C. and 2 hours at room temperature the solution was evaporated, the residue re-dissolved in dichloromethane was washed with saturated NaHCO3 aqueous solution. The organic layers were dried (Na2SO4) and concentrated under vacuum to obtain 900 mg of the title compound.

Workup

custom2 hours at room temperature the solution was evaporated
dissolutionthe residue re-dissolved in dichloromethane
washwas washed with saturated NaHCO3 aqueous solution
dry with materialThe organic layers were dried (Na2SO4)
concentrationconcentrated under vacuum

Sources & evidence

ORD record: ord-4bec20d37dd04371a148673dc83774ca
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08859608B2

Reaction notes

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