1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 10971697, compound

HRID 2306232Notes

Reaction equation

HRID 2306232 reaction equation
[Si:1]([O:18][C:19]1[CH:27]=[C:26]2[C:22]([CH2:23][CH2:24][CH:25]2O)=[CH:21][CH:20]=1)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(P([N:43]=[N+:44]=[N-:45])(C2C=CC=CC=2)=O)C=CC=CC=1.N12CCCN=C1CCCCC2>C1(C)C=CC=CC=1>[Si:1]([O:18][C:19]1[CH:27]=[C:26]2[C:22]([CH2:23][CH2:24][CH:25]2[N:43]=[N+:44]=[N-:45])=[CH:21][CH:20]=1)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 199401P,P-Diphenylphosphinic azideHCID 11760910HCID 11760910, compound

Product 1

HCID 10971697HCID 10971697, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 6-tert-butyldiphenylsilyloxy-1-indanol, as described above in Step B, (5.80 g, 14.9 mmol) and diphenylphosphoryl azide (4.98 g, 18.1 mmol) in toluene (30 mL) at 0° C. was added 1,8-diazabicyclo[5.4.0]undec-7-ene (2.50 mL, 16.4 mmol), dropwise. The mixture was allowed to slowly warm to ambient temperature and was stirred for 18 hours, then washed with H2O (10 mL), then dilute HCl (10 mL), then dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by silica gel chromatography, eluting with hexane—1% EtOAc, to yield the titled product.

Workup

  1. washwashed with H2O (10 mL)
  2. dry with materialdilute HCl (10 mL), then dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by silica gel chromatography
  6. washeluting with hexane—1% EtOAc

Sources & evidence

ORD record
ord-0dc835c4d11f4ec1b8fc9b9e14b333a8
Source dataset
uspto-grants-2002_08
Patent number
US06441017B1

Reaction notes

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