1,8-Diazabicyclo(5.4.0)undec-7-ene → 4(R)-Azido-6,8-dibromo-chroman

HRID 1008959Notes

Reaction equation

HRID 1008959 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([Br:12])[CH:11]=1)[O:8][CH2:7][CH2:6][C@@H:5]2O.C1(P([N:28]=[N+:29]=[N-:30])(C2C=CC=CC=2)=O)C=CC=CC=1.N12CCCN=C1CCCCC2>O1CCCC1.C(OC(=O)C)C>[N:28]([C@H:5]1[C:4]2[C:9](=[C:10]([Br:12])[CH:11]=[C:2]([Br:1])[CH:3]=2)[O:8][CH2:7][CH2:6]1)=[N+:29]=[N-:30]

Participants

6

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 199401P,P-Diphenylphosphinic azideHCID 67304261(S)-6,8-Dibromochroman-4-ol

Product 1

HCID 866200164(R)-Azido-6,8-dibromo-chroman

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution containing 6,8-dibromo-chroman-4(S)-ol in tetrahydrofuran (0.17M) and 1.2 equivalents of diphenylphosphorylazide was stirred for 15 minutes at room temperature. The solution was cooled to 10° C. and 2.5 equivalents of 1,8-diazabicyclo[5.4.0]undec-7-ene added. The mixture was stirred with gradual warming to room temperature and maintained for 48 h. The mixture was diluted with ethylacetate and washed with brine followed by water. The organic phase was concentrated to afford the title compound as a tan oil.

Workup

  1. temperatureThe solution was cooled to 10° C.
  2. stirringThe mixture was stirred
  3. temperaturewith gradual warming to room temperature
  4. temperaturemaintained for 48 h
  5. washwashed with brine
  6. concentrationThe organic phase was concentrated

Sources & evidence

ORD record
ord-a7dbc9ef49184c28889d6fa51a957303
Source dataset
uspto-grants-2011_07
Patent number
US07973050B2

Reaction notes

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