4-(Trifluoromethoxy)aniline → 8-(2,2-Dimethyl-propane-1-sulfonyl)-2-(4-trifluoromethoxy-phenyl)-2,8-diaza-spiro[4.5]decan-1-one

HRID 2194016Notes

Reaction equation

HRID 2194016 reaction equation
C([O:3][C:4]([C:6]1([CH2:20][CH2:21]OC)[CH2:11][CH2:10][N:9]([S:12]([CH2:15][C:16]([CH3:19])([CH3:18])[CH3:17])(=[O:14])=[O:13])[CH2:8][CH2:7]1)=O)C.[Cl-].C[Al+]C.[F:28][C:29]([F:39])([F:38])[O:30][C:31]1[CH:37]=[CH:36][C:34]([NH2:35])=[CH:33][CH:32]=1>CCCCCCC>[CH3:18][C:16]([CH3:17])([CH3:19])[CH2:15][S:12]([N:9]1[CH2:8][CH2:7][C:6]2([C:4](=[O:3])[N:35]([C:34]3[CH:36]=[CH:37][C:31]([O:30][C:29]([F:38])([F:39])[F:28])=[CH:32][CH:33]=3)[CH2:21][CH2:20]2)[CH2:11][CH2:10]1)(=[O:13])=[O:14]

Participants

5

Reactant 3

HCID 6008484-(Trifluoromethoxy)anilineHCID 16686359Dimethylalumanylium chlorideHCID 667872401-(2,2-Dimethyl-propane-1-sulfonyl)-4-(2-methoxy-ethyl)-piperidine-4-carboxylic acid ethyl ester

Product 1

HCID 498022468-(2,2-Dimethyl-propane-1-sulfonyl)-2-(4-trifluoromethoxy-phenyl)-2,8-diaza-spiro[4.5]decan-1-oneYield 54.1%

Reagents, catalysts & solvents 1

HCID 8900HeptaneSolvent

Procedure

This material was prepared in analogy to example 1 step D) 1-(2,2-dimethyl-propane-1-sulfonyl)-4-(2-methoxy-ethyl)-piperidine-4-carboxylic acid ethyl ester (0.17 g), dimethylaluminium chloride in heptane (1.0 molar, 1.46 ml) and 4-(trifluoromethoxy)-aniline (0.129 g) to give the desired 8-(2,2-dimethyl-propane-1-sulfonyl)-2-(4-trifluoromethoxy-phenyl)-2,8-diaza-spiro[4.5]decan-1-one (0.118 g) as an off-white solid. MS (ESI): 449.17 (MH+).

Sources & evidence

ORD record
ord-b0d8d47bb80a4c73bcd0a87b99bd43c9
Source dataset
uspto-grants-2012_12
Patent number
US08329904B2

Reaction notes

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