Methanol → cyclohexane carboxylic acid N'-isopropyl-hydrazide

A solution of methyl-cyclohexane carboxylate (20 g, 140.65 mmol) and hydrazine monohydrate (35 ml, 703.25 mmol) in MeOH (100 ml) was refluxed overnight. The mixture was concentrated to dryness and the residue was partitioned between saturated aqueous sodium bicarbonate and DCM. The organic layer was washed with brine, dried over sodium sulfate, filtered and concentrated (14.35 g, 75%). A portion of the resulting hydrazide 1 (2.6 g, 18.28 mmol) was dissolved in acetone (100 ml) and the solution was refluxed overnight. The solution was concentrated to dryness. The residue was dissolved in TFA (30 ml) and treated with triethylsilane (5.83 ml, 36.56 mmol) at 60° C. overnight. The reaction mixture was concentrated under reduced pressure and the residue was partitioned between 1N NaOH and DCM. The organic layer was washed with brine, dried over sodium sulfate and concentrated under vacuum to afford the product as a white solid (2.0 g, 61%).

1. concentrationThe mixture was concentrated to dryness
2. customthe residue was partitioned between saturated aqueous sodium bicarbonate and DCM
3. washThe organic layer was washed with brine
4. dry with materialdried over sodium sulfate
5. filtrationfiltered
6. concentrationconcentrated (14.35 g, 75%)
7. temperaturethe solution was refluxed overnight
8. concentrationThe solution was concentrated to dryness
9. dissolutionThe residue was dissolved in TFA (30 ml)
10. concentrationThe reaction mixture was concentrated under reduced pressure
11. customthe residue was partitioned between 1N NaOH and DCM
12. washThe organic layer was washed with brine
13. dry with materialdried over sodium sulfate
14. concentrationconcentrated under vacuum

ORD record

ord-e24da515d2694c3886bf892a72bcfc4c

Source dataset

uspto-grants-2008_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07317125B2