1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 18401884, compound

HRID 1018663Notes

Reaction equation

HRID 1018663 reaction equation
C1(COC2C=CC3C(O)CCCCC=3C=2)CCCCC1.C1CCN2C(=NCCC2)CC1.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.[N:49]([CH:52]1[C:58]2[CH:59]=[CH:60][C:61]([O:63][CH2:64][CH:65]3[CH2:70][CH2:69][CH2:68][CH2:67][CH2:66]3)=[CH:62][C:57]=2[CH2:56][CH2:55][CH2:54][CH2:53]1)=[N+:50]=[N-:51].C1(COC2C=CC3C=CCCCC=3C=2)CCCCC1>C1(C)C=CC=CC=1.CCOC(C)=O>[N:49]([CH:52]1[C:58]2[CH:59]=[CH:60][C:61]([O:63][CH2:64][CH:65]3[CH2:70][CH2:69][CH2:68][CH2:67][CH2:66]3)=[CH:62][C:57]=2[CH2:56][CH2:55][CH2:54][CH2:53]1)=[N+:50]=[N-:51]

Participants

7

Reactant 4

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 199401P,P-Diphenylphosphinic azideHCID 18401893HCID 18401893, compoundHCID 86585965HCID 86585965, compound

Product 1

HCID 18401884HCID 18401884, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To 2-cyclohexylmethoxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-5-ol (14.2 g, 52.0 mmol) in toluene (100 mL) at 0° C. was added DBU (9.4 mL, 62.9 mmol) followed by diphenylphosphoryl azide (13.6 mL, 62.9 mmol). The mixture was allowed to stir for 18 h at rt, diluted with EtOAc, then washed successively with 1 N HCl, and water. The organic layer was dried over MgSO4, filtered, concentrated, and chomatographed over silica gel (5% EtOAc/hexane) to yield a 7:3 mixture of 5-azido-2-cyclohexylmethoxy-6,7,8,9-tetrahydro-5H-benzocycloheptene/3-cyclohexylmethoxy-6,7-dihydro-5H-benzocycloheptene (12.6 g). This mixture was used without further purification in the next reaction.

Workup

  1. washwashed successively with 1 N HCl, and water
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto yield
  6. customThis mixture was used without further purification in the next reaction

Sources & evidence

ORD record
ord-65094fee4916495485170592acd0d099
Source dataset
uspto-grants-2002_11
Patent number
US06482852B2

Reaction notes

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