Triphenylphosphine → HCID 178461791, compound

HRID 2368151Notes

Reaction equation

HRID 2368151 reaction equation
O[C@@H:2]1[CH2:7][CH2:6][C@H:5]([O:8][CH2:9][C@@H:10]([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[CH3:11])[CH2:4][CH2:3]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P([N:53]=[N+:54]=[N-:55])(C2C=CC=CC=2)=O)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1(C)C=CC=CC=1>[N:53]([C@H:2]1[CH2:7][CH2:6][C@H:5]([O:8][CH2:9][C@@H:10]([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[CH3:11])[CH2:4][CH2:3]1)=[N+:54]=[N-:55]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 199401P,P-Diphenylphosphinic azideHCID 178461792HCID 178461792, compound

Product 1

HCID 178461791HCID 178461791, compoundYield 19.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

To a solution of tert-butyl {(1S)-2-[(cis-4-hydroxycyclohexyl)oxy]-1-methylethyl}carbamate (5.00 g), triphenylphosphine (7.20 g) and diphenylphosphorylazide (5.03 g) in toluene (200 mL) was added dropwise a solution (1.9 M, 14.4 mL) of diisopropyl azodicarboxylate in toluene, and the mixture was stirred at room temperature for 16 hr. The reaction mixture was concentrated under reduced pressure, the residue was suspended in diethyl ether, and the precipitate was removed by filtration. The filtrate was concentrated, and the residue was purified by silica gel chromatography(hexane/ethyl acetate) to give the title compound (1.05 g).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe precipitate was removed by filtration
  3. concentrationThe filtrate was concentrated
  4. customthe residue was purified by silica gel chromatography(hexane/ethyl acetate)

Sources & evidence

ORD record
ord-57b64a15732745ae8b33fd338f72c816
Source dataset
uspto-grants-2014_04
Patent number
US08703758B2

Reaction notes

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