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

HRID 916320Notes

Reaction equation

HRID 916320 reaction equation
[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

Participants

4

Reactant 2

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

Product 1

HCID 69224044HCID 69224044, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-c49b1741b9194d6a9f61f85857724a47
Source dataset
uspto-grants-2007_09
Patent number
US07268232B2

Reaction notes

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