Diethyl 4-((hydroxyimino)(4-methoxyphenyl)methyl)benzylphosphonate → Diethyl 4-(amino(4-methoxyphenyl)methyl)benzylphosphonate

HRID 1525314Notes

Reaction equation

HRID 1525314 reaction equation
O[N:2]=[C:3]([C:19]1[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=1)[C:4]1[CH:18]=[CH:17][C:7]([CH2:8][P:9](=[O:16])([O:13][CH2:14][CH3:15])[O:10][CH2:11][CH3:12])=[CH:6][CH:5]=1>CCO.[Ni]>[NH2:2][CH:3]([C:19]1[CH:20]=[CH:21][C:22]([O:25][CH3:26])=[CH:23][CH:24]=1)[C:4]1[CH:5]=[CH:6][C:7]([CH2:8][P:9](=[O:16])([O:13][CH2:14][CH3:15])[O:10][CH2:11][CH3:12])=[CH:17][CH:18]=1

Participants

4

Reactant 1

HCID 131733145Diethyl 4-((hydroxyimino)(4-methoxyphenyl)methyl)benzylphosphonate2×

Product 1

HCID 89462706Diethyl 4-(amino(4-methoxyphenyl)methyl)benzylphosphonateYield 92%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

Diethyl 4-((hydroxyimino)(4-methoxyphenyl)methyl)benzylphosphonate, 32-e, (450 mg, 1.2 mmol) was dissolved in EtOH (10 ml), Raney Ni (50 mg) was added, and the resulting mixture was then stirred for 12 h at ambient temperature under hydrogen. The solution was filtered, filtrate was concentrated under reduce pressure, purified by column chromatography (DCM/MeOH=20:1). The product was obtained as a white solid, 32-f, (400 mg, 92%). 1H NMR (300 MHz, CDCl3) δ 1.18-1.23 (t, J=6.9 Hz 6H), 2.27 (s, 2H), 3.04-3.11 (d, J=21.6 Hz 2H) 3.74 (s, 3H), 3.93-3.99 (m, 4H), 5.12 (s, 1H), 6.78-6.81 (d, J=8.7 Hz, 2H), 7.18-7.28 (m, 6H). LC-MS 364 [MH]+.

Workup

  1. filtrationThe solution was filtered
  2. concentrationfiltrate was concentrated
  3. custompurified by column chromatography (DCM/MeOH=20:1)

Sources & evidence

ORD record
ord-2f2e6b0f8f074eef84153700bd475ee4
Source dataset
uspto-grants-2015_07
Patent number
US09079930B2

Reaction notes

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