Rac-1-(1-oxo-4-phenyl-2,8-diaza-spiro [4.5]dec-8-yl)-cyclohexanecarbonitrile → 4-Phenyl-8-(1-phenyl-cyclohexyl)-2,8-diaza-spiro[4.5]decan-1-one

HRID 914936Notes

Reaction equation

HRID 914936 reaction equation
[O:1]=[C:2]1[C:6]2([CH2:11][CH2:10][N:9]([C:12]3([C:18]#N)[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]3)[CH2:8][CH2:7]2)[CH:5]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:4][NH:3]1.[C:26]1([Mg]Br)[CH:31]=[CH:30]C=[CH:28][CH:27]=1>C1COCC1>[C:20]1([CH:5]2[C:6]3([CH2:7][CH2:8][N:9]([C:12]4([C:18]5[CH:30]=[CH:31][CH:26]=[CH:27][CH:28]=5)[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]4)[CH2:10][CH2:11]3)[C:2](=[O:1])[NH:3][CH2:4]2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

4

Reactant 2

HCID 69486548Rac-1-(1-oxo-4-phenyl-2,8-diaza-spiro [4.5]dec-8-yl)-cyclohexanecarbonitrileHCID 178418255HCID 178418255, compound

Product 1

HCID 113726714-Phenyl-8-(1-phenyl-cyclohexyl)-2,8-diaza-spiro[4.5]decan-1-oneYield 94%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of rac-1-(1-oxo-4-phenyl-2,8-diaza-spiro[4.5]dec-8-yl)-cyclohexanecarbonitrile (400 mg, 1.2 mmol) in dry THF (12 mL) under argon at 0° C. was added phenylmagnesium bromide (1 M in THF, 3.5 mL, 3.6 mmol) and the resulting mixture allowed to warm up to room temperature overnight. The reaction was quenched by the addition of ammonium chloride solution (sat., 20 mL) and the product extracted with ethyl acetate (2×50 mL). The combined organic extracts were then washed with brine (50 mL), dried over sodium sulfate, filtered and evaporated. The residue was purified by chromatography on silica gel eluting with DCM:MeOH:NH4OH (95:4.5:0.5) to afford the title compound (430 mg, 94%) as a white solid. MS: m/e=389.3 (M+H).

Workup

  1. customThe reaction was quenched by the addition of ammonium chloride solution (sat., 20 mL)
  2. extractionthe product extracted with ethyl acetate (2×50 mL)
  3. washThe combined organic extracts were then washed with brine (50 mL)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by chromatography on silica gel eluting with DCM:MeOH:NH4OH (95:4.5:0.5)

Sources & evidence

ORD record
ord-be4beed46ce84bf79157aefbc5da94f1
Source dataset
uspto-grants-2007_09
Patent number
US07265126B2

Reaction notes

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