Sodium Hydroxide → 9-Amino-7-methylidenebicyclo[3.3.1]nonan-3-one

HRID 70495Notes

Reaction equation

HRID 70495 reaction equation
C(OC(=O)[NH:7][CH:8]1[CH:15]2[CH2:16][C:11]3(Br)[CH2:12][C:13](Br)([CH2:17][CH:9]1[CH2:10]3)[CH2:14]2)(C)(C)C.[OH-:21].[Na+]>O1CCOCC1>[NH2:7][CH:8]1[CH:15]2[CH2:14][C:13](=[CH2:12])[CH2:17][CH:9]1[CH2:10][C:11](=[O:21])[CH2:16]2

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 16100375(5,7-Dibromo-adamantan-2-yl)-carbamic acid tert-butyl ester

Product 1

HCID 672127729-Amino-7-methylidenebicyclo[3.3.1]nonan-3-oneYield 163.7%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

(First step: Rohde, J. J. et al. Discovery and Metabolic Stabilization of Potent and Selective 2-Amino-N-(adamant-2-yl) Acetamide 11β-Hydroxysteroid Dehydrogenase Type 1 Inhibitors. J. Med. Chem. 2007, 50, 149-64). A solution of 25 (125 mg, 0.305 mmol) in dioxane (0.80 mL) was treated with 2N NaOH (0.70 mL, 1.37 mmol) and irradiated under microwaves (μw, Biotage) for 15 min at 180° C. The dioxane was removed in vacuo. The residue was dissolved in DCM, washed with water, dried (Na2SO4), filtered and concentrated in vacuo to afford 82.5 mg of crude 9-amino-7-methylene-bicyclo[3.3.1]nonan-3-one as a yellow oil, that was used for the next step without further purification.

Workup

  1. customirradiated under microwaves (μw, Biotage) for 15 min at 180° C
  2. customThe dioxane was removed in vacuo
  3. dissolutionThe residue was dissolved in DCM
  4. washwashed with water
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d66d71b2214d4d26b6d3016f98981c61
Source dataset
uspto-grants-2014_09
Patent number
US08822541B2

Reaction notes

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