HCID 88932544, compound → HCID 86671474, compound

HRID 1530642Notes

Reaction equation

HRID 1530642 reaction equation
[F:1][C:2]([F:14])([F:13])/[CH:3]=[N:4]/[NH:5][C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7]>CO.[Pd]>[F:1][C:2]([F:13])([F:14])[CH2:3][NH:4][NH:5][C:6]([O:8][C:9]([CH3:10])([CH3:11])[CH3:12])=[O:7]

Participants

4

Reactant 1

HCID 88932544HCID 88932544, compound

Product 1

HCID 86671474HCID 86671474, compoundYield 33%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of (E)-tert-butyl 2-(2,2,2-trifluoroethylidene)hydrazinecarboxylate (4.00 g, 18.9 mmol) and 20% Pd/C (2.00 g) in MeOH (20.0 mL) was stirred under H2 atmosphere at 25° C. for 16 h. The solid was filtered off and the filtrate was evaporated to give the crude product, which was purified by silica gel chromatography eluting with EtOAc/petroleum ether (1:100) to afford tert-butyl 2-(2,2,2-trifluoroethyl)hydrazinecarboxylate (1.32 g, 33% yield) as pale yellow oil. LCMS (ESI) m/z: 159.3 [M-56+H+].

Workup

  1. filtrationThe solid was filtered off
  2. customthe filtrate was evaporated
  3. customto give the crude product, which
  4. customwas purified by silica gel chromatography
  5. washeluting with EtOAc/petroleum ether (1:100)

Sources & evidence

ORD record
ord-80abc4fc87794512bde8d3988d39a79e
Source dataset
uspto-grants-2015_07
Patent number
US09090628B2

Reaction notes

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