HCID 22850139, compound → HCID 22850137, compound

HRID 865841Notes

Reaction equation

HRID 865841 reaction equation
[N:1]([CH2:4][C@H:5]([OH:15])[CH2:6][P:7]([CH3:14])(=[O:13])[O:8][CH2:9][CH:10]([CH3:12])[CH3:11])=[N+]=[N-].[H][H]>C(O)C.[Pd]>[NH2:1][CH2:4][C@H:5]([OH:15])[CH2:6][P:7]([CH3:14])(=[O:13])[O:8][CH2:9][CH:10]([CH3:12])[CH3:11]

Participants

5

Reactant 2

HCID 22850139HCID 22850139, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 22850137HCID 22850137, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 1.2 g of isobutyl P-[3-azido-2(S)- hydroxy-propyl]-P-methyl-phosphinate in 25 ml of ethanol are added 0.25 g of 5% palladium on charcoal. The resulting mixture is hydrogenated at 1 bar until hydrogen uptake ceases. The mixture is then filtered and the filtrate evaporated to give isobutyl P-[3-amino-2(S)-hydroxy-propyl]-P-(methyl)-phosphinate as a viscous oil, 31P-NMR spectrum: δ=+55.6 and +54.6 ppm (CDCl3), [α]D25 =+10.9 (c=0.50% in ethanol).

Workup

  1. filtrationThe mixture is then filtered
  2. customthe filtrate evaporated

Sources & evidence

ORD record
ord-18541933a384442a9a5dd5a5d21ce2ec
Source dataset
uspto-grants-1996_10
Patent number
US05567840

Reaction notes

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