1-(4-Chlorobenzyl)-7-cyclohexyl-1,7-diazaspiro[4.4]nonane-3,6-dione → 1-(4-Chlorobenzyl)-7-cyclohexyl-3-hydroxy-3-methyl-1,7-diazaspiro[4.4]nonan-6-one

HRID 1672395Notes

Reaction equation

[CH3:1]C(=C)C[Mg]Cl.[Cl:7][C:8]1[CH:31]=[CH:30][C:11]([CH2:12][N:13]2[C:17]3([CH2:21][CH2:20][N:19]([CH:22]4[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]4)[C:18]3=[O:28])[CH2:16][C:15](=[O:29])[CH2:14]2)=[CH:10][CH:9]=1>C1COCC1>[Cl:7][C:8]1[CH:9]=[CH:10][C:11]([CH2:12][N:13]2[C:17]3([CH2:21][CH2:20][N:19]([CH:22]4[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]4)[C:18]3=[O:28])[CH2:16][C:15]([OH:29])([CH3:1])[CH2:14]2)=[CH:30][CH:31]=1

Participants

Conditions

Temperature: 50 °C

Procedure

2-Methylallylmagnesium chloride in THF (3.0 M, 0.074 mL) was added to a solution of 1-(4-chlorobenzyl)-7-cyclohexyl-1,7-diazaspiro[4.4]nonane-3,6-dione (0.040 g, 0.00011 mol) in THF (1.0 mL, 0.012 mol) and the resulting mixture was stirred at 50° C. for 1 h. The reaction mixture was then allowed to cool to RT and was then quenched by the addition of saturated NH4Cl. The crude reaction mixture was purified by prep. HPLC to afford the desired product. LC/MS: 377.2 (M+1H)+.

Workup

temperatureto cool to RT
customwas then quenched by the addition of saturated NH4Cl
customThe crude reaction mixture
customwas purified by prep

Sources & evidence

ORD record: ord-80b753a146c34d1dbd5a5a21ce81fd5c
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07998959B2

Reaction notes

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