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1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 68679502, compound

HRID 2353978
Notes
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Reaction equation

HRID 2353978 reaction equation
C(OC(N1C2C(=CC3OC(F)(F)OC=3C=2)[C@H](O)CCC1)=O)(C)(C)C.C1C=CC(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)=CC=1.C1CCN2C(=NCCC2)CC1.[C:53]([O:57][C:58]([N:60]1[C:73]2[C:65](=[CH:66][C:67]3[O:68][C:69]([F:75])([F:74])[O:70][C:71]=3[CH:72]=2)[C@@H:64]([N:76]=[N+]=[N-])[CH2:63][CH2:62][CH2:61]1)=[O:59])([CH3:56])([CH3:55])[CH3:54]>C1(C)C=CC=CC=1.CO.[Pd]>[C:53]([O:57][C:58]([N:60]1[C:73]2[C:65](=[CH:66][C:67]3[O:68][C:69]([F:75])([F:74])[O:70][C:71]=3[CH:72]=2)[C@@H:64]([NH2:76])[CH2:63][CH2:62][CH2:61]1)=[O:59])([CH3:56])([CH3:54])[CH3:55]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 199401P,P-Diphenylphosphinic azideHCID 68679478HCID 68679478, compoundHCID 86616084(S)-9-Azido-2,2-difluoro-6,7,8,9-tetrahydro-1,3-dioxa-5-aza-cyclohepta[f]indene-5-carboxylic acid tert-butyl ester

Product 1

HCID 68679502HCID 68679502, compound

Reagents, catalysts & solvents

3
HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 1140TolueneSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of (R)-2,2-Difluoro-9-hydroxy-6,7,8,9-tetrahydro-1,3-dioxa-5-aza-cyclohepta[f]indene-5-carboxylic acid tert-butyl ester (1.9 mmol) in Toluene, add DPPA (2.5 mmol) and DBU (2.5 mmol). After heating the mixture at 65° C. for 14 h, remove solvent under vacuum and chromatograph the intermediate using ethyl acetate/hexane (5-20%) to elute. This provides (S)-9-Azido-2,2-difluoro-6,7,8,9-tetrahydro-1,3-dioxa-5-aza-cyclohepta[f]indene-5-carboxylic acid tert-butyl ester as a colorless oil. To a solution of (S)-9-Azido-2,2-difluoro-6,7,8,9-tetrahydro-1,3-dioxa-5-aza-cyclohepta[f]indene-5-carboxylic acid tert-butyl ester (1.8 mmol) in methanol (20 mL) add a catalytic amount of Pd/C after purging the solution with nitrogen. Place a balloon of hydrogen on the reaction and purge the solution several times. After stirring for 1 h, purge the solution with nitrogen then filter through celite. Collect the filtrate and remove solvent under vacuum to provide the title compound as a colorless oil.

Workup

  1. customremove solvent under vacuum and chromatograph the intermediate
  2. washto elute
  3. customafter purging the solution with nitrogen
  4. customon the reaction
  5. custompurge the solution several times
  6. custompurge the solution with nitrogen
  7. filtrationthen filter through celite
  8. customCollect the filtrate
  9. customremove solvent under vacuum

Sources & evidence

ORD record
ord-021bfb81ccc3447fb6f8ad890a9eee85
Source dataset
uspto-grants-2010_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07749992B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes