(3-Dibenzylamino-2-hydroxy-5-methyl-hexyl)-phosphonic acid dimethyl ester → Phosphonic acid, P-(3-amino-2-hydroxy-5-methylhexyl)-, dimethyl ester

HRID 43311Notes

Reaction equation

HRID 43311 reaction equation
[CH3:1][O:2][P:3]([CH2:7][CH:8]([OH:29])[CH:9]([N:14](CC1C=CC=CC=1)CC1C=CC=CC=1)[CH2:10][CH:11]([CH3:13])[CH3:12])(=[O:6])[O:4][CH3:5]>CO.[C].[Pd]>[CH3:1][O:2][P:3]([CH2:7][CH:8]([OH:29])[CH:9]([NH2:14])[CH2:10][CH:11]([CH3:12])[CH3:13])(=[O:6])[O:4][CH3:5]

Participants

4

Reactant 1

HCID 72266810(3-Dibenzylamino-2-hydroxy-5-methyl-hexyl)-phosphonic acid dimethyl ester

Product 1

HCID 72266813Phosphonic acid, P-(3-amino-2-hydroxy-5-methylhexyl)-, dimethyl ester

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Conditions

Temperature
39.5 °C

Procedure

Reaction 4: A diastereomeric mixture of the crude (3-dibenzylamino-2-hydroxy-5-methyl-hexyl)-phosphonic acid dimethyl ester, compound 4, obtained in reaction 3, was treated with palladium-carbon (2.0% wt) as the catalyst in methanol (40 mL). The mixture reaction was stirred for 12 h under a hydrogen gas atmosphere at 37-42° C., and after this period of time, the mixture was filtered through a pad of Celite, and the solvents were removed under reduced pressure to leave (3-amino-2-hydroxy-5-methyl-hexyl)-phosphonic acid dimethyl ester, compound 5 as a crude oil.

Workup

  1. customReaction 4
  2. customobtained in reaction 3
  3. customThe mixture reaction
  4. waitafter this period of time
  5. filtrationthe mixture was filtered through a pad of Celite
  6. customthe solvents were removed under reduced pressure

Sources & evidence

ORD record
ord-c4e19fb0a02840b997b434a444db0e99
Source dataset
uspto-grants-2013_09
Patent number
US08536362B2

Reaction notes

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