tert-Butanol → HCID 178453943, compound

HRID 2079592Notes

Reaction equation

HRID 2079592 reaction equation
[C:1]([C@H:3]1[CH2:8][CH2:7][C@H:6](C(O)=O)[CH2:5][CH2:4]1)#[N:2].C([N:14]([CH2:17]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:26])C=CC=CC=1.C(OCC)(=O)C.[C:42]([OH:46])([CH3:45])([CH3:44])[CH3:43]>>[C:1]([C@H:3]1[CH2:4][CH2:5][C@H:6]([NH:14][C:17](=[O:26])[O:46][C:42]([CH3:45])([CH3:44])[CH3:43])[CH2:7][CH2:8]1)#[N:2]

Participants

6

Reactant 5

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 199401P,P-Diphenylphosphinic azideHCID 178511260HCID 178511260, compound

Product 1

HCID 178453943HCID 178453943, compoundYield 54%

Procedure

To a solution of 765 mg (4.99 mmol) of trans-4-cyanocyclohexane carboxylic acid in 10 mL of tert-butanol was added 766 μL (5.49 mmol) of triethylamine and 1.13 mL (5.24 mmol) of diphenylphosphorylazide at room temperature, and the mixture was refluxed for 6 hours. After the reaction mixture was cooled to room temperature, ethyl acetate was added to this mixture and the organic layer was washed with saturated sodium bicarbonate aqueous solution, then, dried over with anhydrous sodium sulfate. The solvent was removed under reduced pressure and the residue was purified by silica gel column chromatography (eluent:hexane/ethyl acetate=2/1) to give 608 mg (54%) of the title compound.

Workup

  1. temperaturethe mixture was refluxed for 6 hours
  2. washthe organic layer was washed with saturated sodium bicarbonate aqueous solution
  3. dry with materialdried over with anhydrous sodium sulfate
  4. customThe solvent was removed under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (eluent:hexane/ethyl acetate=2/1)

Sources & evidence

ORD record
ord-a53eaf691cf94b7d8f06956d8085b682
Source dataset
uspto-grants-2011_04
Patent number
US07932250B2

Reaction notes

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