HCID 54534282, compound → HCID 54388314, compound

HRID 1884032Notes

Reaction equation

HRID 1884032 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10](=[O:25])[CH2:11][CH:12]([CH2:18][CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:6][CH:5]=1)([O-])=O>[Pd].C(O)C>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([C:10](=[O:25])[CH2:11][CH:12]([CH2:18][CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:8][CH:9]=1

Participants

4

Reactant 1

HCID 54534282HCID 54534282, compound

Product 1

HCID 54388314HCID 54388314, compoundYield 79.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of diethyl (RS)-2-(2-(4-nitrophenyl)-2-oxoethyl)glutarate (1.48 g, 4.2 mmol) and 10% palladium on carbon (0.23 g) in ethanol (100 ml) was shaken under hydrogen (30-35 psi)for 40 minutes. The catalyst was filtered off and the filtrate concentrated in vacuo. Purification by chromatography on silica gel eluting with ethyl acetate:hexane (1:1) gave diethyl (RS)2-(2-(4-aminophenyl)-2-oxoethyl)glutarate (1.07 g) as an oil that solidified on standing. M.P. 58-61° C. 1H NMR (DMSO-d6), 200 MHz) δ: 1.13 (t, J=7 Hz, 3H, CH3), 1.16 (t, J=7 Hz, 3H, CH3), 1.67-1.87 (m, 2H, CH2), 2.28-2.40 (m, 2H, CH2CO2), 2.72-2.88 (m, 1H, CH), 2.99 (ABX, apparent JAB=17.5 Hz, JAX=4.5 Hz, 1H, COCH—H), 3.19 (ABX, apparent JAB=17.5 Hz, JBX=9.5 Hz, 1H, COCH—H), 4.00 (q, J=7 Hz, 2H, esterCH2), 4.03 (q, J=7 Hz, 2H, esterCH2), 6.04 (br s, 2H, NH2), 6.53 (d, J=9 Hz, 2H, Ar), 7.66 (d, J=9 Hz, 2H Ar). Mass spectrum (CI-CH4): 322 (M+1, 94.4%), 276 (100%). Anal. Calculated for C17H23NO5.0.15H2O: C, 63.01; H, 7.25; N, 4.32. Found: C, 62.98; H, 7.24; N, 4.28.

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate concentrated in vacuo
  3. customPurification by chromatography on silica gel eluting with ethyl acetate:hexane (1:1)

Sources & evidence

ORD record
ord-7aff152eb693499e94994d48af91a2fe
Source dataset
uspto-grants-2004_07
Patent number
US06762188B1

Reaction notes

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