Trifluoroacetic acid → Benzyl 1,6-diazaspiro[3.5]nonane-1-carboxylate
Reaction equation
C(OC([N:8]1[CH2:26][CH2:25][CH2:24][C:10]2([N:13]([C:14]([O:16][CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[O:15])[CH2:12][CH2:11]2)[CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O.[OH-].[Na+]>C(Cl)(Cl)Cl>[CH2:17]([O:16][C:14]([N:13]1[C:10]2([CH2:24][CH2:25][CH2:26][NH:8][CH2:9]2)[CH2:11][CH2:12]1)=[O:15])[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1Participants
Procedure
To a solution of an optically-active compound of 1,6-diazaspiro[3,5]-nonane-1,6-dicarboxylic acid 1-benzyl ester 6-tert-butyl ester (5.35 g) in chloroform (134 ml) cooled to 0° C. was added trifluoroacetic acid (27 ml), and the mixture was stirred for 30 minutes, warmed to room temperature and stirred for additional 30 minutes. The reaction mixture was cooled to 0° C., and thereto was added 4M aqueous sodium hydroxide solution (91 ml). The aqueous layer was extracted with chloroform (100 ml, 50 ml) twice, and the combined organic layer was washed with saturated aqueous sodium chloride solution and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent: chloroform/methanol=20/1 to 4/1) to give the titled compound (2.37 g).
Workup
- stirringstirred for additional 30 minutes
- temperatureThe reaction mixture was cooled to 0° C.
- extractionThe aqueous layer was extracted with chloroform (100 ml, 50 ml) twice
- washthe combined organic layer was washed with saturated aqueous sodium chloride solution
- concentrationconcentrated under reduced pressure
- customThe resulting residue was purified by silica gel column chromatography (eluent: chloroform/methanol=20/1 to 4/1)
Sources & evidence
- ORD record
- ord-8d3626b262c140a89b70d7b10a22d4f5
- Source dataset
- uspto-grants-2013_12
- Patent number
- US08609647B2
Reaction notes
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