Trifluoroacetic acid → Ammonia

HRID 1266974Notes

Reaction equation

HRID 1266974 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([N:10]2[CH:16]3[CH2:17][CH2:18][CH:11]2[CH2:12][N:13](C(OC(C)(C)C)=O)[CH2:14][CH2:15]3)[CH:7]=[N:8][CH:9]=1)[CH3:2].F[C:27](F)(F)[C:28]([OH:30])=[O:29].[OH-:33].[Na+]>ClCCl>[NH3:8].[C:28]([OH:30])(=[O:29])/[CH:27]=[CH:2]/[C:1]([OH:3])=[O:33].[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([N:10]2[CH:16]3[CH2:17][CH2:18][CH:11]2[CH2:12][NH:13][CH2:14][CH2:15]3)[CH:7]=[N:8][CH:9]=1)[CH3:2]

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 120512859-[5-Ethoxy-(3-pyridyl)]-3-tert-butoxycarbonyl-3,9-diazabicyclo-[4.2.1]-nonane

Product 2

HCID 222AmmoniaHCID 1317238639-[5-Ethoxy-(3-pyridyl)]-3,9-diazabicyclo-[4.2.1]-nonane Fumaric Acid Salt

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 9-[5-ethoxy-(3-pyridyl)]-3-tert-butoxycarbonyl-3,9-diazabicyclo-[4.2.1]-nonane (0.23 g, 0.66 mmol), trifluoroacetic acid (0.75 g, 6.6 mmol) and dichloromethane (10 ml) was stirred for 3 days at room temperature. Sodium hydroxide (20 ml, 1M) was added and the phases were separated, followed by extraction with dichloromethane (20 ml). Chromatography on silica gel with dichloromethane, methanol and conc. ammonia (89:10:1) gave the title compound. The corresponding salt was obtained, by addition of a diethyl ether and methanol mixture (9:1) saturated with fumaric acid. Yield 0.39 g, 21%. Mp. 191-192° C.

Workup

  1. customthe phases were separated
  2. extractionfollowed by extraction with dichloromethane (20 ml)

Sources & evidence

ORD record
ord-9403aadff51f4984b8148d2bac593325
Source dataset
uspto-grants-2003_04
Patent number
US06552012B2

Reaction notes

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