1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 59846403, compound

HRID 1363230Notes

Reaction equation

HRID 1363230 reaction equation
C1CCN2C(=NCCC2)CC1.[F:12][C:13]1[CH:22]=[C:21]2[C:16]([CH2:17][CH2:18][CH2:19][C@@H:20]2O)=[CH:15][CH:14]=1.C1(P([N:38]=[N+:39]=[N-:40])(C2C=CC=CC=2)=O)C=CC=CC=1>C1(C)C=CC=CC=1.C(Cl)Cl>[N:38]([C@H:20]1[C:21]2[C:16](=[CH:15][CH:14]=[C:13]([F:12])[CH:22]=2)[CH2:17][CH2:18][CH2:19]1)=[N+:39]=[N-:40]

Participants

6

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 199401P,P-Diphenylphosphinic azideHCID 282938631083302-30-0

Product 1

HCID 59846403HCID 59846403, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

DBU (27.1 mL, 180.5 mmol, 3 equiv.) was added to a solution of (S)-7-Fluoro-1,2,3,4-tetrahydronaphthalen-1-ol (10 g, 60.2 mmol, 1 equiv.) in toluene (300 mL). The resulted dark red solution was cooled in ice bath. Diphenylphosphoryl azide (38.6 mL, 180.6 mmol, 3 equiv) was added drop-wise within 30 min. The reaction solution was slowly brought to RT and stirred overnight. TLC was checked and showed no more SM. The reaction was diluted with methylene chloride (200 mL). The methylene chloride layer was washed with saturated NaHCO3, brine, water, saturated NH4Cl, and brine. The organic layer was separated and dried (Na2SO4), evaporated under reduced pressure to give a dark-red syrup which was purified on ISCO (80 g column, 0-2% EtOAc-hexane) to give a colorless oil product (7.9 g, 70%). 1H NMR (400 MHz, CDCl3) δ 7.07-7.11 (m, 1H), 7.02 (dd, 1H), 6.91-6.96 (m, 1H), 4.51 (t, 1H), 2.69-2.86 (m, 2H), 1.76-2.05 (m, 4H).

Workup

  1. temperatureThe resulted dark red solution was cooled in ice bath
  2. customwas slowly brought to RT
  3. washThe methylene chloride layer was washed with saturated NaHCO3, brine, water, saturated NH4Cl, and brine
  4. customThe organic layer was separated
  5. dry with materialdried (Na2SO4)
  6. customevaporated under reduced pressure
  7. customto give a dark-red syrup which
  8. customwas purified on ISCO (80 g column, 0-2% EtOAc-hexane)

Sources & evidence

ORD record
ord-3e43acec2b2c441691ce69ee213c000e
Source dataset
uspto-grants-2011_02
Patent number
US07884109B2

Reaction notes

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