Benzyl 2-(di-tert-butoxyphosphoryloxy)ethyl(ethyl)carbamate → Di-tert-butyl 2-(ethylamino)ethyl phosphate

HRID 1771184Notes

Reaction equation

HRID 1771184 reaction equation
[C:1]([O:5][P:6]([O:13][CH2:14][CH2:15][N:16]([CH2:27][CH3:28])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:13][CH2:14][CH2:15][NH:16][CH2:27][CH3:28])([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])([O:8][C:9]([CH3:10])([CH3:11])[CH3:12])=[O:7]

Participants

4

Reactant 1

HCID 58080156Benzyl 2-(di-tert-butoxyphosphoryloxy)ethyl(ethyl)carbamate2×

Product 1

HCID 58080210Di-tert-butyl 2-(ethylamino)ethyl phosphateYield 94%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Benzyl 2-(di-tert-butoxyphosphoryloxy)ethyl(ethyl)carbamate (INTERMEDIATE 48, 0.9 g, 2.17 mmol) was dissolved in methanol (5 ml), and 5% Pd on charcoal (0.10 g) was added. The reaction mixture was stirred at r.t under a hydrogen atmosphere overnight. The reaction mixture was filtered and concentrated in vacuo to give the title compound (0.57 g, yield: 94%).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1bc93118b80b431ba72e5b3b0430ac70
Source dataset
uspto-grants-2016_02
Patent number
US09248140B2

Reaction notes

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