Ethanol → 4-(Propan-2-yl)-1,4-azaphosphinane 4-oxide oxalate salt

HRID 1039984Notes

Reaction equation

HRID 1039984 reaction equation
C([N:8]1[CH2:13][CH2:12][P:11](=[O:17])([CH:14]([CH3:16])[CH3:15])[CH2:10][CH2:9]1)C1C=CC=CC=1.C(O)C.O.O.[C:23]([OH:28])(=[O:27])[C:24]([OH:26])=[O:25]>O.[Pd]>[C:23]([OH:28])(=[O:27])[C:24]([OH:26])=[O:25].[CH3:15][CH:14]([P:11]1(=[O:17])[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]1)[CH3:16]

Participants

6

Reactant 3

HCID 702EthanolHCID 61373Oxalic acid dihydrateHCID 674329511-Benzyl-4-(propan-2-yl)-1,4-azaphosphinane 4-oxide

Product 1

HCID 674302504-(Propan-2-yl)-1,4-azaphosphinane 4-oxide oxalate saltYield 53%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

A 10 L auto clave was charged with the product of Step 2 (200.0 g, 796.8 mmol), ethanol (4000 mL) and oxalic acid dihydrate (100.4 g, 797.0 mmol) in water (1000 ml). To the reaction mixture was added palladium on carbon (10% w/w, 99.6 g) and stirred at room temperature under H2 pressure (50 psi) for 16 h. After completion, the reaction mixture filtered and concentrated. Obtained solid was triturated with hot ethanol (250 mL) and kept in a cold room for 90 minutes, filtered, washed with diethylether and hexane to give 4-(propan-2-yl)-1,4-azaphosphinane 4-oxide oxalate salt (105 g, 53%) as a colorless solid. Mp 223-224° C. LC ESI: [M]+ m/z 162. HPLC (ELSD method)=99.9%.

Workup

  1. filtrationAfter completion, the reaction mixture filtered
  2. concentrationconcentrated
  3. customObtained solid
  4. customwas triturated with hot ethanol (250 mL)
  5. waitkept in a cold room for 90 minutes
  6. filtrationfiltered
  7. washwashed with diethylether and hexane

Sources & evidence

ORD record
ord-b3fa18d80c8c4e468b93634adcb7be44
Source dataset
uspto-grants-2013_10
Patent number
US08551984B2

Reaction notes

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