HCID 59323318, compound → HCID 86712680, compound

HRID 1779032Notes

Reaction equation

HRID 1779032 reaction equation
[OH:1][CH2:2][CH2:3][N:4]([CH2:12][C:13]1[CH:18]=[CH:17][C:16]([N+:19]([O-])=O)=[CH:15][CH:14]=1)[C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8]>CCOC(C)=O.[Pd]>[NH2:19][C:16]1[CH:15]=[CH:14][C:13]([CH2:12][N:4]([CH2:3][CH2:2][OH:1])[C:5](=[O:11])[O:6][C:7]([CH3:9])([CH3:10])[CH3:8])=[CH:18][CH:17]=1

Participants

4

Reactant 1

HCID 59323318HCID 59323318, compound

Product 1

HCID 86712680HCID 86712680, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A suspension of tert-butyl (2-hydroxyethyl)(4-nitrobenzyl)carbamate (A69) (2.40 g, 8.09 mmol) and 10% Pd/C (0.240 g) in EtOAc (12 mL) was stirred under a hydrogen atmosphere for 18 hours. The resulting mixture was filtered through a pad of Celite, washing with EtOAc and the filtrate concentrated in vacuo. The residue was purified using silica gel column chromatography (CombiFlash Rf, 40 g SiO2 cartridge, 20-50% EtOAc in cyclohexane) to give the title compound A70 as a viscous light yellow oil (1.99 g, 92%); 1H NMR (300 MHz, CDCl3) δ 7.05 (d, J=7.5 Hz, 2H), 6.66 (d, J=8.0 Hz, 2H), 4.37 (s, 2H), 3.67 (m, 4H), 3.37 (s, 2H), 3.10 (s, 1H), 1.50 (s, 9H).

Workup

  1. filtrationThe resulting mixture was filtered through a pad of Celite
  2. washwashing with EtOAc
  3. concentrationthe filtrate concentrated in vacuo
  4. customThe residue was purified

Sources & evidence

ORD record
ord-8afa3449c87f4d6c9fa275e5a2bd2712
Source dataset
uspto-grants-2016_02
Patent number
US09266864B2

Reaction notes

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