Trifluoroacetic acid → 2,8-Diazaspiro[4.5]decan-1-one, 4-(4-fluorophenyl)-

HRID 347307Notes

Reaction equation

C(OC([N:8]1[CH2:25][CH2:24][C:11]2([C:15](=[O:16])[NH:14][CH2:13][CH:12]2[C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O.[OH-].[Na+]>C(Cl)Cl>[F:23][C:20]1[CH:21]=[CH:22][C:17]([CH:12]2[C:11]3([CH2:10][CH2:9][NH:8][CH2:25][CH2:24]3)[C:15](=[O:16])[NH:14][CH2:13]2)=[CH:18][CH:19]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 4-(4-fluoro-phenyl)-1-oxo-2,8-diaza-spiro[4.5]decane-8-carboxylic acid tert-butyl ester (46.0 g, 132 mmol) in DCM (260 mL) containing TFA (150 mL, 1.32 mol) was stirred vigorously at 0° C. for 15 min. The reaction mixture was then poured into NaOH (3 N, 200 mL) and the product extracted with DCM (3×100 mL). The combined organic extracts were then washed with water (100 mL) and brine (100 mL) and then dried over sodium sulfate. Filtration and evaporation afforded the title compound (22.14 g, 68%) as a white solid after trituration from ethyl acetate. MS: m/e=249.2 (M+H).

Workup

extractionthe product extracted with DCM (3×100 mL)
washThe combined organic extracts were then washed with water (100 mL) and brine (100 mL)
dry with materialdried over sodium sulfate
filtrationFiltration and evaporation

Sources & evidence

ORD record: ord-a4a8b216717c4c10af17803d57ee0104
Source dataset: uspto-grants-2007_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07173133B2

Reaction notes

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