2-(4-Nitrobenzyl)-1,3,2-dioxaphosphinane 2-oxide → 2-(4-Aminobenzyl)-1,3,2-dioxaphosphorinane-2-oxide

HRID 1948038Notes

Reaction equation

HRID 1948038 reaction equation
[N+:1]([C:4]1[CH:17]=[CH:16][C:7]([CH2:8][P:9]2(=[O:15])[O:14][CH2:13][CH2:12][CH2:11][O:10]2)=[CH:6][CH:5]=1)([O-])=O>C1COCC1.[Pd]>[O:15]=[P:9]1([CH2:8][C:7]2[CH:16]=[CH:17][C:4]([NH2:1])=[CH:5][CH:6]=2)[O:10][CH2:11][CH2:12][CH2:13][O:14]1

Participants

4

Reactant 1

HCID 113458932-(4-Nitrobenzyl)-1,3,2-dioxaphosphinane 2-oxide2×

Product 1

HCID 112991132-(4-Aminobenzyl)-1,3,2-dioxaphosphorinane-2-oxideYield 81.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 2-(4-nitrobenzyl)-1,3,2-dioxaphosphinane 2-oxide (Compound 230D, 70 mg, 0.27 mmol) in anhydrous THF was added 10% Pd/C (10 mg). The resulting mixture was heated at 50° C. under 50 psi H2 atmosphere for 6 h. Catalyst was filtered off and the filtrate was concentrated to give the desired product (50 mg, yield: 80%). 1H NMR (CD3OD, 400 MHz): δ=1.72-1.76 (m, 1H), 1.98-2.02 (m, 1H), 3.19 (d, J=20.4 Hz, 2H), 4.28-4.40 (m, 4H), 6.68 (d, J=8.0 Hz, 2H), 7.03 (d, J=8.4 Hz, 2H).

Workup

  1. filtrationCatalyst was filtered off
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-1eabd93c5625442988bda0312fb2fd4d
Source dataset
uspto-grants-2013_03
Patent number
US08399433B2

Reaction notes

Loading…