Triphenylphosphine → Di-tert-butyl 1-[(4,4-difluorocyclohexyl)methyl]hydrazine-1,2-dicarboxylate

HRID 69122Notes

Reaction equation

[F:1][C:2]1([F:10])[CH2:7][CH2:6][CH:5]([CH2:8]O)[CH2:4][CH2:3]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[N:30]([C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])=[N:31][C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33]>C1(C)C=CC=CC=1>[F:1][C:2]1([F:10])[CH2:7][CH2:6][CH:5]([CH2:8][N:30]([C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])[NH:31][C:32]([O:34][C:35]([CH3:36])([CH3:37])[CH3:38])=[O:33])[CH2:4][CH2:3]1

Participants

Conditions

Temperature: 12.5 °C

Procedure

To 3.9 g of (4,4-difluorocyclohexyl)methanol was added 40 mL of toluene. 10.2 g of triphenylphosphine was added thereto at room temperature, followed by stirring for a while. The mixture was ice-cooled, and 7.2 g of di-tert-butyl azodicarboxylate was portionwise added thereto while maintaining the internal temperature at about 10 to 15° C. The reaction mixture was stirred at room temperature for 20 hours. The solvent was evaporated and the residue was purified by silica gel column chromatography (n-hexane/ethyl acetate) to obtain 10.7 g of di-tert-butyl 1-[(4,4-difluorocyclohexyl)methyl]hydrazine-1,2-dicarboxylate.

Workup

customat room temperature
temperaturecooled
stirringThe reaction mixture was stirred at room temperature for 20 hours
customThe solvent was evaporated
customthe residue was purified by silica gel column chromatography (n-hexane/ethyl acetate)

Sources & evidence

ORD record: ord-89e1e1af0dc34422b4dabf8a04c2c76f
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08822448B2

Reaction notes

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