HCID 88932543, compound → HCID 57600137, compound

HRID 1530623Notes

Reaction equation

HRID 1530623 reaction equation
[Si:1]([O:8][CH2:9]/[CH:10]=[N:11]/[NH:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]>CO.[Pd]>[Si:1]([O:8][CH2:9][CH2:10][NH:11][NH:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 88932543HCID 88932543, compound

Product 1

HCID 57600137HCID 57600137, compoundYield 55%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of (E)-tert-butyl 2-(2-(tert-butyldimethylsilyloxy)ethylidene)hydrazinecarboxylate (5.1 g, 17.71 mmol) and Pd/C (0.5 g, 10%) in MeOH (100 mL) was stirred under 1 atm H2 at room temperature for 1 h. The solid was filtered off and the filtrate was concentrated. The residue was purified by silica gel chromatography eluting with EtOAc/petroleum ether (5:1) to give tert-butyl 2-(2-(tert-butyldimethylsilyloxy)ethyl)hydrazinecarboxylate (2.8 g, 55% yield) as colorless oil. LCMS (ESI) m/z: 235.3 [M-56+H+].

Workup

  1. filtrationThe solid was filtered off
  2. concentrationthe filtrate was concentrated
  3. customThe residue was purified by silica gel chromatography
  4. washeluting with EtOAc/petroleum ether (5:1)

Sources & evidence

ORD record
ord-e5c4cd9b5f0141b9b765b59fc802e567
Source dataset
uspto-grants-2015_07
Patent number
US09090628B2

Reaction notes

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