Triisopropyl phosphite → HCID 86745100, compound

HRID 728891Notes

Reaction equation

HRID 728891 reaction equation
[C:1]([O:5][C:6]([N:8]1[C@H:12]([CH:13]=[CH:14][CH2:15][CH2:16][CH2:17]Br)[CH2:11][O:10][C:9]1([CH3:20])[CH3:19])=[O:7])([CH3:4])([CH3:3])[CH3:2].[P:21]([O:30]C(C)C)([O:26][CH:27]([CH3:29])[CH3:28])[O:22][CH:23]([CH3:25])[CH3:24]>>[C:1]([O:5][C:6]([N:8]1[C@H:12]([CH:13]=[CH:14][CH2:15][CH2:16][CH2:17][P:21]([O:26][CH:27]([CH3:29])[CH3:28])([O:22][CH:23]([CH3:25])[CH3:24])=[O:30])[CH2:11][O:10][C:9]1([CH3:20])[CH3:19])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 8304Triisopropyl phosphiteHCID 57107979HCID 57107979, compound

Product 1

HCID 86745100HCID 86745100, compound

Procedure

A solution of 19.9 g of bromide 4 according to d) in 60 ml of triisopropyl phosphite is heated at 130°-135° for 20 hours at 100 mbar. The excess reagent is distilled off at 60°/0.1 mbar, and the residue is chromatographed on 250 g of silica gel. Elution with hexane/ethyl acetate 1:1 yields 20.6 g of phosphonic acid ester 5, [α]D =-8.6° (c=0.8, CHCl3); C21H40NO6P; calculated: C 58.18%, H 9.30%, N 3.23%, P 7.15%; found: C 57.4%, H 9.3%, N 3.2%, P 7.5%.

Workup

  1. distillationThe excess reagent is distilled off at 60°/0.1 mbar
  2. customthe residue is chromatographed on 250 g of silica gel
  3. washElution with hexane/ethyl acetate 1:1

Sources & evidence

ORD record
ord-0d67847e33964ae3a05e6faedd4a611a
Source dataset
uspto-grants-1991_09
Patent number
US05051413

Reaction notes

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