Benzyl 2-(di-tert-butoxyphosphoryloxy)ethylcarbamate → 2-Aminoethyl di(tert-butyl) phosphate

HRID 2238447

Reaction equation

HRID 2238447 reaction equation
[C:1]([O:5][P:6]([O:13][CH2:14][CH2:15][NH:16]C(=O)OCC1C=CC=CC=1)([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[P:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])([O:8][C:9]([CH3:10])([CH3:12])[CH3:11])([O:13][CH2:14][CH2:15][NH2:16])=[O:7]

Participants

4

Reactant 1

HCID 68635482Benzyl 2-(di-tert-butoxyphosphoryloxy)ethylcarbamate

Product 1

HCID 862404572-Aminoethyl di(tert-butyl) phosphateYield 79%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 225 (1.17 g, 3.02 mmol) in MeOH (30 mL) with Pd/C (5%, 0.21 g) was hydrogenated at 50 psi for 2.5 h. The mixture was filtered through Celite, washing with MeOH, and the filtrate was evaporated. The residue was dissolved in CH2Cl and the solution was filtered once more, then evaporated to give 2-aminoethyl di(tert-butyl) phosphate (226) (604 mg, 79%) as a colourless oil: 1H NMR [CDCl3] δ 4.01-3.94 (m, 2H), 2.96-2.90 (m, 2H), 1.58 (br s, 2H), 1.49 (s, 18H). HRMS (FAB) calcd. for C10H25NO4P (MH+) m/z 254.1521, found 254.1519.

Workup

  1. filtrationThe mixture was filtered through Celite
  2. washwashing with MeOH
  3. customthe filtrate was evaporated
  4. dissolutionThe residue was dissolved in CH2Cl
  5. filtrationthe solution was filtered once more
  6. customevaporated

Sources & evidence

ORD record
ord-1822e72c026842a18ad49259fc79ee86
Source dataset
uspto-grants-2010_05
Patent number
US07718688B2

Linked notes

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