Cerium trichloride → 8-Hydroxy-8-(prop-1-en-2-yl)-2-(4-(trifluoromethyl)phenyl)-2-aza-spiro[4.5]decan-1-one

HRID 2092701Notes

Reaction equation

HRID 2092701 reaction equation
[F:1][C:2]([F:22])([F:21])[C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:13][CH2:12][C:11]3([CH2:18][CH2:17][C:16](=[O:19])[CH2:15][CH2:14]3)[C:10]2=[O:20])=[CH:5][CH:4]=1.[C:23]([Mg]Br)([CH3:25])=[CH2:24].Cl[Ce](Cl)Cl>>[OH:19][C:16]1([C:23]([CH3:25])=[CH2:24])[CH2:15][CH2:14][C:11]2([C:10](=[O:20])[N:9]([C:6]3[CH:7]=[CH:8][C:3]([C:2]([F:1])([F:21])[F:22])=[CH:4][CH:5]=3)[CH2:13][CH2:12]2)[CH2:18][CH2:17]1

Participants

4

Reactant 3

HCID 161282Cerium trichlorideHCID 582301722-(4-Trifluoromethyl-phenyl)-2-aza-spiro[4.5]decane-1,8-dione2×HCID 178456138HCID 178456138, compound

Product 1

HCID 582299498-Hydroxy-8-(prop-1-en-2-yl)-2-(4-(trifluoromethyl)phenyl)-2-aza-spiro[4.5]decan-1-one

Procedure

The title compound was prepared in analogy to example 55 from 2-(4-trifluoromethyl-phenyl)-2-aza-spiro[4.5]decane-1,8-dione (product of example 208, step 2) by reaction with isopropenylmagnesium bromide (0.5 M in THF), but without use of anhydrous cerous(III)-chloride in the reaction, as a light yellow solid. MS (m/e): 353 [M F].

Sources & evidence

ORD record
ord-452506a4765f486498878e5892c9db03
Source dataset
uspto-grants-2013_05
Patent number
US08440710B2

Reaction notes

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