Triphenylphosphine → HCID 21874358, compound

HRID 73557Notes

Reaction equation

HRID 73557 reaction equation
[N:1]([CH:4]1[CH:9](O)[CH2:8][CH2:7][N:6]([C:11]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[O:12])[CH2:5]1)=[N+]=[N-].N(C1CCN(C(OCC2C=CC=CC=2)=O)CC1O)=[N+]=[N-].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>O1CCOCC1>[CH:4]12[NH:1][CH:9]1[CH2:8][CH2:7][N:6]([C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12])[CH2:5]2

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 17917865HCID 17917865, compoundHCID 59455704HCID 59455704, compound

Product 1

HCID 21874358HCID 21874358, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of benzyl 3-azido-4-hydroxypiperidine-1-carboxylate and benzyl 4-azido-3-hydroxypiperidine-1-carboxylate (1.0 equiv.) in dioxane (0.14M) was added PPh3 (2.0 equiv.) and the reaction was heated to reflux for 1 h. The solution was then concentrated under vacuo and purified via silica gel column chromatography eluting with DCM, 10% MeOH and 1% Et3N to give benzyl 3,7-diazabicyclo[4.1.0]heptane-3-carboxylate as a clear oil in 25% yield. LCMS (m/z): 233.0 (MH+), Rt=1.94 min.

Workup

  1. temperaturethe reaction was heated
  2. temperatureto reflux for 1 h
  3. concentrationThe solution was then concentrated under vacuo
  4. custompurified via silica gel column chromatography
  5. washeluting with DCM, 10% MeOH and 1% Et3N

Sources & evidence

ORD record
ord-19d6db04d5b346ff9f35c6c88aa0fd46
Source dataset
uspto-grants-2014_09
Patent number
US08829193B2

Reaction notes

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