Triphenylphosphine → HCID 178514615, compound

HRID 715565Notes

Reaction equation

HRID 715565 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[CH2:13][CH2:12][C@H:11](O)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(OC(N=NC(OC(C)(C)C)=O)=O)(C)(C)C.C1(P([N:64]=[N+:65]=[N-:66])(C2C=CC=CC=2)=O)C=CC=CC=1>O1CCCC1.C(OCC)C>[N:64]([C@@H:11]1[CH2:12][CH2:13][C@H:8]([C:5]2[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][CH:4]=2)[CH2:9][CH2:10]1)=[N+:65]=[N-:66]

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 97268Di-tert-butyl azodicarboxylateHCID 199401P,P-Diphenylphosphinic azideHCID 178521543HCID 178521543, compound

Product 1

HCID 178514615HCID 178514615, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-5 °C

Procedure

(trans)-4-(4-Bromophenyl)cyclohexanol (500 mg) is dissolved under argon in tetrahydrofurane (8 mL) and cooled to −5° C. Triphenylphosphine (770 mg) and di-tert-butyl-azodicarboxylate (550 mg) are added and the mixture is stirred for 5 minutes. A solution of diphenylphosphorylazide (650 μL) in tetrahydrofurane (8 mL) is added dropwise during 2 hours and the mixture is stirred at 0° C. for 48 hours. Then the mixture is diluted with diethylether, washed with saturated aqueous NaHCO3 solution and the organic phase is dried (MgSO4) and concentrated. The residue is chromatographed on silica gel (petrole ether/ethyl acetate 99:1→70:30) to give the title compound. LC (method 4): tR=0.97 min.

Workup

  1. stirringthe mixture is stirred at 0° C. for 48 hours
  2. washwashed with saturated aqueous NaHCO3 solution
  3. dry with materialthe organic phase is dried (MgSO4)
  4. concentrationconcentrated
  5. customThe residue is chromatographed on silica gel (petrole ether/ethyl acetate 99:1→70:30)

Sources & evidence

ORD record
ord-ccf1cbe6900b4de896304a7677865596
Source dataset
uspto-grants-2015_11
Patent number
US09187477B2

Reaction notes

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