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 914936노트

반응식

HRID 914936 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-be4beed46ce84bf79157aefbc5da94f1
출처 데이터셋
uspto-grants-2007_09
특허 번호
US07265126B2

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