Ethyl Acetate → 2-Amino-2-methylpropyl di-tert-butyl phosphate

HRID 884015Notes

Reaction equation

HRID 884015 reaction equation
[C:1]([O:5][P:6]([O:13][CH2:14][C:15]([NH:18]C(=O)OCC1C=CC=CC=1)([CH3:17])[CH3:16])([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(OCC)(=O)C.[H][H]>[OH-].[OH-].[Pd+2].CO>[P:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])([O:13][CH2:14][C:15]([NH2:18])([CH3:17])[CH3:16])=[O:7]

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 67040944Benzyl 1-(di-tert-butoxyphosphoryloxy)-2-methylpropan-2-ylcarbamateHCID 178418361HCID 178418361, compound

Product 1

HCID 866155662-Amino-2-methylpropyl di-tert-butyl phosphateYield 94.8%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

The product of Example 95B (0.40 g, 0.96 mmol) and 20% palladium hydroxide on carbon (0.21 g) in a ethyl acetate (10 mL) and methanol (1 mL) was stirred under a an atmosphere of hydrogen for 0.5 hours. The reaction was filtered through a bed of celite and concentrate to give the title product (0.256 g).

Workup

  1. filtrationThe reaction was filtered through a bed of celite
  2. concentrationconcentrate

Sources & evidence

ORD record
ord-d2caa09872094c2db9006585af748727
Source dataset
uspto-grants-2012_08
Patent number
US08236950B2

Reaction notes

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