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

HRID 2194014Notes

Reaction equation

HRID 2194014 reaction equation
C(O[C:4]([C:6]1([CH2:19][CH2:20]OC)[CH2:11][CH2:10][N:9]([S:12]([CH2:15][CH:16]([CH3:18])[CH3:17])(=[O:14])=[O:13])[CH2:8][CH2:7]1)=[O:5])C.[Cl-].C[Al+]C.[F:27][C:28]([F:38])([F:37])[O:29][C:30]1[CH:36]=[CH:35][C:33]([NH2:34])=[CH:32][CH:31]=1>CCCCCCC>[CH3:18][CH:16]([CH3:17])[CH2:15][S:12]([N:9]1[CH2:8][CH2:7][C:6]2([C:4](=[O:5])[N:34]([C:33]3[CH:35]=[CH:36][C:30]([O:29][C:28]([F:27])([F:37])[F:38])=[CH:31][CH:32]=3)[CH2:20][CH2:19]2)[CH2:11][CH2:10]1)(=[O:13])=[O:14]

Participants

5

Reactant 3

HCID 6008484-(Trifluoromethoxy)anilineHCID 16686359Dimethylalumanylium chlorideHCID 667870884-(2-Methoxy-ethyl)-1-(2-methyl-propane-1-sulfonyl)-piperidine-4-carboxylic acid ethyl ester

Product 1

HCID 498022458-(2-Methyl-propane-1-sulfonyl)-2-(4-trifluoromethoxy-phenyl)-2,8-diaza-spiro[4.5]decan-1-oneYield 77.2%

Reagents, catalysts & solvents 1

HCID 8900HeptaneSolvent

Procedure

This material was prepared in analogy to example 1 step D) 4-(2-methoxy-ethyl)-1-(2-methyl-propane-1-sulfonyl)-piperidine-4-carboxylic acid ethyl ester (0.134 g), dimethylaluminium chloride in heptane (1.0 molar, 1.2 ml) and 4-(trifluoromethoxy)-aniline (0.106 g) to give the desired 8-(2-methyl-propane-1-sulfonyl)-2-(4-trifluoromethoxy-phenyl)-2,8-diaza-spiro[4.5]decan-1-one (0.134 g) as an off-white solid. MS (ESI): 435.15 (MH+).

Sources & evidence

ORD record
ord-9ebe408655ec4e768601cfbe50940024
Source dataset
uspto-grants-2012_12
Patent number
US08329904B2

Reaction notes

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