Trifluoroacetic acid → 2-Methyl-4-pyridin-3-yl-2,7-diaza-spiro[4.5]decan-1-one

HRID 1036724Notes

Reaction equation

C(OC([N:8]1[CH2:25][CH2:24][CH2:23][C:10]2([C:14](=[O:15])[N:13]([CH3:16])[CH2:12][CH:11]2[C:17]2[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=2)[CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:16][N:13]1[CH2:12][CH:11]([C:17]2[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=2)[C:10]2([CH2:23][CH2:24][CH2:25][NH:8][CH2:9]2)[C:14]1=[O:15]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 2-Methyl-1-oxo-4-pyridin-3-yl-2,7-diaza-spiro[4.5]decane-7-carboxylic acid tert-butyl ester [from diastereomer 1] (200 mg, 0.58 mmol) in DCM (5 ml) was cooled with an ice bath and TFA (0.70 ml, 8.68 mmol) was added. The resulting solution was stirred for 3 h at 0° C. The reaction mixture was diluted with DCM (20 ml) and quenched at 0° C. with 2M NaOH solution (8 ml). The organic phase was separated, washed with brine (5 ml), dried (MgSO4) and concentrated in vacuo to afford the title compound as a yellow oil.

Workup

customquenched at 0° C. with 2M NaOH solution (8 ml)
customThe organic phase was separated
washwashed with brine (5 ml)
dry with materialdried (MgSO4)
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-3b8640776e5c4a5aac88dd18f1368ce6
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08546416B2

Reaction notes

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