4-(3-Oxo-8-azabicyclo[3.2.1]octan-8-yl)naphthalene-1-carbonitrile → HCID 69224044, 화합물

HRID 916320노트

반응식

HRID 916320 반응식
[O:1]1[CH2:6][CH2:5][CH2:4][O:3][CH:2]1[CH2:7][CH2:8][Mg]Br.[O:11]=[C:12]1[CH2:18][CH:17]2[N:19]([C:20]3[C:29]4[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=4)[C:23]([C:30]#[N:31])=[CH:22][CH:21]=3)[CH:14]([CH2:15][CH2:16]2)[CH2:13]1>C1COCC1>[O:1]1[CH2:6][CH2:5][CH2:4][O:3][CH:2]1[CH2:7][CH2:8][C:12]1([OH:11])[CH2:13][CH:14]2[N:19]([C:20]3[C:29]4[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=4)[C:23]([C:30]#[N:31])=[CH:22][CH:21]=3)[CH:17]([CH2:16][CH2:15]2)[CH2:18]1

참가 물질

4

반응물 2

HCID 247436404-(3-Oxo-8-azabicyclo[3.2.1]octan-8-yl)naphthalene-1-carbonitrileHCID 178419673HCID 178419673, 화합물

생성물 1

HCID 69224044HCID 69224044, 화합물

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

1,3-Dioxane-2-ylethyl magnesium bromide reagent (0.5 M solution in anhydrous THF: 860 μL, 0.43 mmol) was added dropwise to a solution of 156AF03-217 (80 mg, 0.29 mmol) in anhydrous THF (2 mL) at rt. After 48 h stirring at rt the reaction was quenched with saturated ammonium chloride. The mixture was partitioned between ammonium chloride and ethyl acetate. The organic layer was dried over sodium sulfate, filtered and evaporated to dryness. Purification of the residue by silica gel column chromatography, eluting with a stepwise gradient of 40-100% ethyl acetate in n-heptane, afforded the desired compound as a diastereomeric mixture, ratio 85:15 (37 mg, 45%).

후처리

  1. customwas quenched with saturated ammonium chloride
  2. customThe mixture was partitioned between ammonium chloride and ethyl acetate
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated to dryness
  6. customPurification of the residue by silica gel column chromatography
  7. washeluting with a stepwise gradient of 40-100% ethyl acetate in n-heptane

출처 및 근거

ORD 기록
ord-c49b1741b9194d6a9f61f85857724a47
출처 데이터셋
uspto-grants-2007_09
특허 번호
US07268232B2

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